Heteroaryl piperidine and heteroaryl piperazine derivatives as fungicides

ABSTRACT

Heteroarylpiperidine and -piperazine derivatives of the formula (I) 
     
       
         
         
             
             
         
       
     
     in which the symbols A, X, Y, L 1 , L 2 , G, Q, p, R 1 , R 2  and R 10  are each as defined in the description, and salts, metal complexes and N-oxides of the compounds of the formula (I), and the use thereof for controlling phytopathogenic harmful fungi and processes for preparing compounds of the formula (I).

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation application of U.S. application Ser.No. 13/879,876, filed Sep. 23, 2013, which is a §371 National StageApplication of PCT/EP2011/068592, filed Oct. 25, 2011, which claimspriority to European Application No. 10189067.1, filed Oct. 27, 2010 andU.S. Provisional Application 61/407,200, filed Oct. 27, 2010, thecontents of which are incorporated herein by reference in theirentireties.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention relates to heteroarylpiperidine and -piperazinederivatives, to agrochemically active salts thereof, to use thereof andto methods and compositions for controlling phytopathogenic harmfulfungi in and/or on plants or in and/or on seed of plants, to processesfor producing such compositions and treated seed, and to use thereof forcontrolling phytopathogenic harmful fungi in agriculture, horticultureand forestry, in animal health, in the protection of materials and inthe domestic and hygiene sector. The present invention further relatesto a process for preparing heteroarylpiperidine and -piperazinederivatives.

2. Description of Related Art

It is already known that particular heterocyclically substitutedthiazoles can be used as fungicidal crop protection agents (see patentapplications with publication numbers: WO 07/014290, WO 08/013925, WO08/013622, WO 08/091594, WO 08/091580, WO 09/055514, WO 09/094407, WO09/094445, WO 09/132785, WO 10/037479, WO10/065579, WO2010/066353,WO2010/149275, WO2011/051243, WO2011/051244, WO 2011/076510, WO2011/018415, WO 2011/018401, WO 2011/076699; see also patentapplications with application numbers: DE102010000662.9,PCT/EP2011/056594, PCT/EP2011/057912, PCT/EP2011/058330,PCT/EP2011/063783, PCT/EP2011/064527). However, specifically atrelatively low application rates, the fungicidal efficacy of thesecompounds is not always adequate.

Since the ecological and economical demands made on modem cropprotection agents are increasing constantly, for example with respect toactivity spectrum, toxicity, selectivity, application rate, formation ofresidues and favourable manufacture, and there can furthermore beproblems, for example, with resistances, there is a constant need todevelop novel crop protection agents, in particular fungicides, which,at least in some areas, have advantages over the known ones.

It has now been found that, surprisingly, the presentheteroarylpiperidine and -piperazine derivatives achieve at least someaspects of the objects mentioned and are suitable for use as cropprotection agents, especially as fungicides.

SUMMARY

The invention provides compounds of the formula (I)

in which the radicals are each defined as follows:

-   A is phenyl which may contain up to five substituents,    -   where the substituents are each independently selected from        Z^(A-1),-   or-   A is an optionally benzofused, unsubstituted or substituted 5- or    6-membered heteroaryl which may contain up to four substituents,    where the substituents on carbon are each independently selected    from Z^(A-2) and the substituents on nitrogen are each independently    selected from Z^(A-3),-   Z^(A-1) are the same or different and are each independently    hydrogen, halogen, hydroxyl, thioxy, nitro, cyano, —C(═O)H,    —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,    haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl,    halocycloalkenyl, hydroxyalkyl, cyanoalkyl, formylalkyl,    alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkynyloxyalkyl,    alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl,    haloalkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl,    alkylcarbonylalkyl, alkylsulphonylalkyl, alkylcycloalkyl,    alkylcycloalkenyl, alkoxy, alkylcycloalkylalkyl, halocycloalkoxy,    alkylthio, haloalkylthio, cycloalkylthio, alkynylthio, alkenyloxy,    alkynyloxy, haloalkoxy, haloalkenyloxy, haloalkynyloxy, cycloalkoxy,    alkoxyalkoxy, cycloalkylalkoxy, alkylcarbonyloxy,    haloalkylcarbonyloxy, cycloalkylcarbonyloxy, cycloalkylamino,    alkylcarbonylamino, cycloalkylcarbonylamino, alkoxycarbonylamino,    alkylsulphonylamino, haloalkylsulphonylamino, phenylsulphonylamino,    cycloalkylalkyl, halocycloalkylalkyl, cycloalkylcycloalkyl,    alkoxyalkoxyalkyl, alkylaminocarbonyloxy, alkylcarbonylalkoxy,    cycloalkylaminocarbonyl, cycloalkylalkoxycarbonyl, alkylsulphinyl,    haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,    cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl,    cycloalkylcarbonyl, alkoxycarbonyl, cycloalkoxycarbonyl,    trialkylsilyl, —SF₅, phenyl, —C(═O)NR³R⁴ or —NR³R⁴,-   Z^(A-2) and R^(G1) are the same or different and are each    independently hydrogen, halogen, hydroxyl, thioxy, nitro, cyano,    —C(═O)H, —C(═O)OH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,    haloalkynyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, formylalkyl,    alkoxyalkyl, alkylcarbonylalkyl, alkylcycloalkyl, alkoxy,    alkylcycloalkylalkyl, alkylthio, haloalkylthio, alkynylthio,    alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy,    haloalkylcarbonyloxy, cycloalkylcarbonylamino, alkylsulphonylamino,    haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl,    halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxycarbonyloxy,    alkylcarbonylthio, alkylsulphinyl, haloalkylsulphinyl,    alkylsulphonyl, haloalkylsulphonyl, alkylcarbonyl,    haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy,    —C(═O)NR³R⁴ or —NR³R⁴,-   Z^(A-3), R^(G2) and Z² are the same or different and are each    independently hydrogen, —C(═O)H, —C(═O)NR³R⁴, alkyl, alkenyl,    alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,    halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl,    alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl,    phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,    haloalkoxycarbonyl, cycloalkoxycarbonyl, phenyl or benzyl,-   R³ and R⁴ are the same or different and are each independently    hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or    phenyl,-   L¹ is NR^(L12) or C(R^(L11))₂,-   R^(L11) is the same or different and is independently hydrogen,    halogen, hydroxyl, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl,    alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl,    alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy,    alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy,    alkylcarbonylamino, alkylcarbonylthio, alkylsulphonyl,    haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl,    alkoxycarbonyl, trialkylsilyloxy, —NR³R⁴ or —C(═O)NR³R⁴,    -   or the two R^(L11) radicals, together with the carbon atom to        which they are bonded, form a cyclopropyl ring, or    -   the two R^(L11) radicals are ═CH₂, ═COR³, ═NOR³ or ═CHN(R⁷)₂,-   R^(L12) is hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl, haloalkyl,    haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,    alkylcycloalkyl, cycloalkylalkyl, cycloalkylaminocarbonyl,    haloalkylaminocarbonyl, alkylsulphonyl, haloalkylsulphonyl,    cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl,    alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl,    alkylaminocarbonyl, dialkylaminocarbonyl, phenyl or benzyl,-   R⁷ is alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or    phenyl,-   Y is sulphur or oxygen,-   X is carbon or nitrogen,-   R² is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or    hydroxyl,-   R¹⁰ is oxo, alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or    hydroxyl,-   p is 0, 1 or 2,-   G is 5-membered heteroaryl which is substituted by Q and may    otherwise be unsubstituted or substituted, where the substituents on    carbon are each independently selected from R^(G1) and the    substituents on nitrogen are each independently selected from    R^(G2),-   Q is saturated or partly or fully unsaturated 5-membered    heterocyclyl which is substituted by L²-R¹ and may otherwise be    unsubstituted or substituted, where the substituents are each    independently selected from R⁵,-   R⁵ is the same or different and is independently:    -   bonded to carbon of the 5-membered heterocyclyl of Q:    -   hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)OH,        —C(═O)NH₂, —C(═O)NR³R⁴, —NR³R⁴, alkyl, alkenyl, alkynyl,        haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,        alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl,        halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl,        halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl,        cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl,        formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl,        alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl,        haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl,        haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl,        cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl,        cycloalkylaminocarbonyl, hydroxyalkyl, alkoxy, haloalkoxy,        cycloalkoxy, halocycloalkoxy, cycloalkylalkoxy, alkenyloxy,        haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkoxyalkoxy,        alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy,        alkylcarbonylalkoxy, alkylthio, haloalkylthio, cycloalkylthio,        alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl,        haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl,        alkylsulphonylamino, haloalkylsulphonylamino,    -   bonded to nitrogen of the 5-membered heterocyclyl of Q:    -   hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,        haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl,        cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl, —C(═O)H,        alkoxycarbonyl or alkylcarbonyl,-   L² is a direct bond, 0, C(═O), S(O)_(m), CHR²⁰ or NR²¹,-   m is 0, 1 or 2,-   R²⁰ is hydrogen, alkyl or haloalkyl,-   R²¹ is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl,    haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl,-   R¹ is phenyl which is substituted once by a Z⁴ substituent and may    additionally optionally have further substitution, where these    additional substituents are each independently selected from Z⁴ and    Z′,-   or-   R¹ is naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl,    hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which is    substituted once by a Z⁵ substituent and may additionally optionally    have further substitution, where these additional substituents are    each independently selected from Z⁵ and Z¹,-   or-   R¹ is an optionally benzofused, substituted 5- or 6-membered    heteroaryl which is substituted once, either on a carbon by a Z⁶    substituent or on the nitrogen by a Z⁷ substituent, and may    additionally optionally be substituted by further substituents,    where the additional substituents on the carbon are each    independently selected from Z¹ and Z⁶, and the additional    substituents on the nitrogen are each independently selected from Z²    and Z⁷,-   Z¹ is hydrogen, halogen, hydroxyl, nitro, cyano, alkyl, alkenyl,    alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,    halocycloalkyl, alkoxy, alkoxyalkyl, hydroxyalkyl, haloalkoxy,    alkylcarbonyl, alkoxycarbonyl, alkylcycloalkyl, cycloalkoxyalkyl,    cycloalkylamino, alkylthio, haloalkylthio, cycloalkylthio,    cycloalkylalkyl, alkylcarbonyloxy, alkylcarbonylamino,    haloalkylcarbonylamino, alkylcarbonylthio, alkylsulphinyl,    haloalkylsulphinyl, alkylsulphonyloxy, haloalkylsulphonyloxy,    alkylcycloalkylalkyl, —C(═O)NR³R⁴, —NR³R⁴, or -L³Z³,-   L³ is a direct bond, —CH₂—, —C(═O)—, sulphur, oxygen, —C(═O)O—,    —C(═O)NH—, —OC(═O)— or —NHC(═O)—,-   Z³ is a phenyl radical, naphthalenyl radical or a 5- or 6-membered    heteroaryl radical, each of which may contain 0, 1, 2 or 3    substituents, where the substituents are each independently selected    from the following list:    -   substituents on carbon: halogen, cyano, nitro, hydroxyl, amino,        —SH, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,        haloalkynyl, cycloalkyl, halocycloalkyl, alkoxyalkyl,        alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy,        haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy,        alkynyloxy, alkoxyalkoxy, alkylamino, dialkylamino, alkylthio,        haloalkylthio, alkylsulphinyl, haloalkylsulphinyl,        alkylsulphonyl, haloalkylsulphonyl, trisilylalkyl or phenyl,    -   substituents on nitrogen: hydrogen, —C(═O)H, alkyl, alkenyl,        alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,        halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl,        alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl,        phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl,        alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl,        —C(═O)NR³R⁴, phenyl or benzyl,-   Z⁴ is SH, C(═O)H, C₇-C₈-cycloalkyl, C₇-C₈-halocycloalkyl,    cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl,    halocycloalkenyl, C₄-C₆-alkoxy-C₁-C₄-alkyl, C₃-alkoxy-C₂-C₄-alkyl,    alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl,    alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl,    haloalkylaminoalkyl, cycloalkylaminoalkyl, C₄-C₆-alkylcarbonyl,    haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl,    cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl,    C₅-C₆-hydroxyalkyl, C₅-C₆-alkoxy, C₅-C₆-haloalkoxy, cycloalkoxy,    halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy,    alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy,    haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy,    C₅-C₆-alkylthio, C₅-C₆-haloalkylthio, C₅-C₆-alkylsulphinyl,    C₅-C₆-haloalkylsulphinyl, C₅-C₆-alkylsulphonyl,    C₅-C₆-haloalkylsulphonyl, cycloalkylsulphonyl,    tri(C₃-C₄-alkyl)silyl, alkylsulphonylamino or    haloalkylsulphonylamino,-   Z⁵ is tri(C₂-C₄-alkyl)silyl, benzyl, phenyl, SH, C₅-C₆-alkoxy,    C₅-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,    C₅-C₆-alkylthio or C₅-C₆-haloalkylthio,-   Z⁶ is SH, cycloalkylcycloalkyl or tri(C₃-C₄-alkyl)silyl,-   Z⁷ is alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl,    cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl,    cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl or phenyl,-   and salts, metal complexes and N-oxides of the compounds of the    formula (I),    -   with the proviso that the following compounds are excluded:

-   -   in which the symbols have the following meanings:    -   Y is oxygen or sulphur,    -   R² is hydrogen or halogen,    -   Q is

-   -   R⁵ is hydrogen, cyano, C₁-C₃-alkyl or C₁-C₃-haloalkyl,    -   L² is a direct bond and    -   R¹ is as defined above, where, when R¹ is substituted phenyl,        naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl,        hexahydronaphthalenyl, octahydronaphthalenyl or indenyl or an        optionally benzofused, 5- or 6-membered heteroaryl, not more        than two substituents are present on the carbocycles or        heterocycles mentioned.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The invention further provides for the use of the compounds of theformula (I) as fungicides.

Inventive heteroarylpiperidine and -piperazine derivatives of theformula (I) and the salts, metal complexes and N-oxides thereof are verysuitable for controlling phytopathogenic harmful fungi. Theaforementioned inventive compounds exhibit, in particular, potentfungicidal activity and can be used in crop protection, in the domesticand hygiene sector and in the protection of materials.

The compounds of the formula (I) may be present either in pure form oras mixtures of different possible isomeric forms, especially ofstereoisomers, such as E and Z, threo and erythro, and also opticalisomers, such as R and S isomers or atropisomers, and, if appropriate,also of tautomers. Both the E and Z isomers, and the threo and erythroisomers, and also the optical isomers, any desired mixtures of theseisomers, and the possible tautomeric forms are claimed.

The radical definitions of the inventive compounds of the formula (I)preferably, more preferably and most preferably have the followingdefinitions:

-   A is preferably phenyl which may contain up to two substituents,    where the substituents are each independently selected from the    following list:    -   halogen, cyano, hydroxyl, —NR³R⁴, —C(═O)NR³R⁴, nitro,        C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,        C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,        C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₁-C₄-alkenyloxy, C₁-C₄-alkynyloxy, C₁-C₄-alkylthio,        C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,        C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkoxy-C₁-C₆-alkyl,        hydroxy-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkylcarbonyloxy or —C(═O)H, or-   A is preferably a heteroaromatic radical selected from the following    group: furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl,    isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyrrol-1-yl,    pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl,    thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl,    isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl,    pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,    1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, pyridin-2-yl, pyridin-3-yl,    pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl,    pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl which    may contain up to two substituents, where the substituents are each    independently selected from the following list:    -   substituents on carbon:    -   halogen, cyano, hydroxyl, nitro, —NR³R⁴, C₁-C₆-alkyl,        C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl,        C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl,        C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,        C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio,        C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        hydroxy-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkylcarbonyloxy or phenyl,    -   substituents on nitrogen:    -   C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,        C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,        C₃-C₁₀-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-haloalkylcarbonyl, phenyl,        benzyl, C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylsulphonyl,        phenylsulphonyl, —C(═O)H, or C₁-C₆-alkylcarbonyl,-   A is more preferably phenyl which may contain up to two    substituents, where the substituents are each independently selected    from the following list:    -   fluorine, bromine, iodine, chlorine, cyano, nitro, methyl,        ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl,        chlorofluoromethyl, dichloromethyl, dichlorofluoromethyl,        difluoromethyl, trichloromethyl, trifluoromethyl, cyclopropyl,        ethoxy, 1-methylethoxy, n-propoxy, methoxy, trifluoromethoxy,        difluoromethoxy, 1-methylethylthio, methylthio, ethylthio,        n-propylthio, difluoromethylthio or trifluoromethylthio, or-   A is more preferably a heteroaromatic radical selected from the    following group: furan-2-yl, furan-3-yl, thiophen-2-yl,    thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,    pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl,    oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,    isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl,    pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl,    imidazol-4-yl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, pyridin-2-yl,    pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl,    pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl, which may contain    up to two substituents, where the substituents are the same or    different and are each independently selected from the following    list:    -   substituents on carbon:    -   fluorine, chlorine, bromine, iodine, cyano, nitro, methyl,        ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl,        chlorofluoromethyl, dichloromethyl, dichlorofluoromethyl,        difluoromethyl, trichloromethyl, trifluoromethyl, cyclopropyl,        ethoxy, 1-methylethoxy, n-propoxy, methoxy, trifluoromethoxy,        difluoromethoxy, 1-methylethylthio, methylthio, ethylthio,        n-propylthio, difluoromethylthio, trifluoromethylthio or phenyl,    -   substituents on nitrogen:    -   methyl, ethyl, n-propyl, 1-methylethyl, methylsulphonyl,        trifluoromethylsulphonyl, methylcarbonyl,        trifluoromethylcarbonyl, chloromethylcarbonyl,        2,2-trifluoroethyl, 2,2-difluoroethyl,        2,2-dichloro-2-fluoroethyl, 2-chloro-2-difluoroethyl or        2-chloro-2-fluoroethyl.-   A is most preferably phenyl which may contain up to two    substituents, where the substituents are each independently selected    from the following list:    -   methyl, ethyl, iodine, chlorine, bromine, fluorine, methoxy,        ethoxy, difluoromethyl or trifluoromethyl or-   A is most preferably pyrazol-1-yl which may contain up to two    substituents, where the substituents are each independently selected    from the following list:    -   methyl, ethyl, chlorine, bromine, fluorine or trifluoromethyl,-   R³ and R⁴ are preferably the same or different and are each    independently hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-haloalkyl, C₃-C₈-cycloalkyl, benzyl or phenyl, and more    preferably hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl    or 1,1-dimethylethyl,-   L¹ is preferably C(R^(L11))₂ (more preferably CHR^(L11)) or NR^(L12)    and most preferably CH₂,-   R^(L11) is preferably hydrogen, methyl, ethyl or cyclopropyl,-   or the two R^(L11) radicals, together with the carbon atom to which    they are bonded, form a cyclopropyl ring, or-   the two R^(L11) radicals are ═CHN(R⁷)₂,-   R^(L11) is more preferably hydrogen or methyl,-   R^(L12) is preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₃-C₈-cycloalkyl, C₁-C₄-alkylsulphonyl, C₁-C₄-alkoxycarbonyl, and    more preferably hydrogen or methyl, and most preferably hydrogen,-   R⁷ is preferably the same or different and is independently    C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,    C₃-C₈-cycloalkyl, benzyl or phenyl, and more preferably hydrogen,    methyl, ethyl, n-propyl, 1-methylethyl, n-butyl or    1,1-dimethylethyl,-   Y is preferably oxygen or sulphur and more preferably oxygen,-   X is carbon or nitrogen and preferably carbon,-   R² is preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-alkenyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy, halogen, cyano or hydroxyl, and more    preferably hydrogen, fluorine, chlorine, bromine or hydroxyl, and    most preferably hydrogen or fluorine (and especially only hydrogen),-   R¹⁰ is preferably oxo, C₁-C₄-alkyl, C₁-C₄-alkenyl, C₁-C₄-haloalkyl,    C₁-C₄-alkoxy, halogen, cyano or hydroxyl, and more preferably    fluorine, chlorine, bromine or hydroxyl, and most preferably    fluorine,-   p is preferably 0 to 1, and more preferably 0,-   G is preferably

-   -   where the bond identified by “v” is bonded directly to X and        where the bond identified by “w” is bonded directly to Q,

-   G is more preferably G¹, G² or G³, and most preferably G¹,

-   R^(G1) is preferably hydrogen or halogen and more preferably    hydrogen,

-   Q is preferably

-   -   where the bond identified by “*” is bonded directly to G, and        where the bond identified by “#” is bonded directly to L²,    -   or    -   where the bond identified by “*” is bonded directly to L², and        where the bond identified by “#” is bonded directly to G,

-   Q is more preferably

-   -   where the bond identified by “x” is bonded directly to G, and        the bond identified by “y” is bonded directly to L²,

-   Q is most preferably Q²⁴-3,

-   R⁵ is preferably the same or different and is independently    -   bonded to carbon of the 5-membered heterocyclyl of Q:    -   hydrogen, cyano, —NR³R⁴, C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,        C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl,        C₃-C₈-halocycloalkyl, C₁-C₄-alkyl-C₃-C₈-cycloalkyl,        C₃-C₈-cycloalkyl-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₃-C₈-cycloalkoxy-C₁-C₄-alkyl,        C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,        C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,        C₃-C₈-cycloalkoxy, C₃-C₈-halocycloalkoxy,        C₃-C₈-cycloalkyl-C₁-C₄-alkoxy, C₂-C₆-alkenyloxy,        C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-haloalkynyloxy,        C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonyloxy,        C₁-C₆-haloalkylcarbonyloxy, C₃-C₈-cycloalkylcarbonyloxy,        C₁-C₆-alkylcarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkylthio,        C₁-C₆-haloalkylthio, C₃-C₈-cycloalkylthio,    -   bonded to nitrogen of the 5-membered heterocyclyl of Q:    -   hydrogen, —C(═O)H, C₁-C₃-alkyl, C₁-C₆-alkylcarbonyl,        C₁-C₆-alkoxycarbonyl or benzyl,

-   R⁵ is more preferably hydrogen, cyano, methyl, trifluoromethyl,    difluoromethyl or methoxymethyl, or

-   R⁵ is most preferably hydrogen,

-   L² is preferably a direct bond, —O—, —C(═O)—, —S(O)_(m)—, —CHR²⁰— or    —NR²¹—, and more preferably a direct bond, —C(═O)—, —CHR²⁰— or    —NR²¹— and most preferably L² is a direct bond,

-   m is preferably 0 or 2,

-   R²⁰ is preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, and more    preferably hydrogen, methyl, ethyl, trifluoromethyl,

-   R²¹ is preferably hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl    or C₁-C₆-haloalkoxycarbonyl, and more preferably hydrogen or methyl,

-   R¹ is preferably phenyl which is substituted once by a Z⁴    substituent and may additionally optionally have further    substitution, where the additional substituents are each    independently selected from Z⁴ and Z¹⁻¹ or

-   R¹ is preferably naphthalen-1-yl, naphthalen-2-yl,    1,2,3,4-tetrahydronaphthalen-1-yl,    1,2,3,4-tetrahydronaphthalen-2-yl,    5,6,7,8-tetrahydronaphthalen-1-yl,    5,6,7,8-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl,    1H-inden-1-yl, 2,3-dihydro-1H-inden-1-yl, 1H-inden-2-yl,    1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl,    1H-inden-7-yl, indan-1-yl, indan-2-yl, indan-3-yl, indan-4-yl or    indan-5-yl,

-   where each of these is substituted once by a Z⁵ substituent and may    additionally optionally have further substitution, where the    additional substituents are each independently selected from Z⁵ and    Z¹², or

-   R¹ is preferably a 5- or 6-membered heteroaryl radical which is    substituted once, either on a carbon by a Z⁶ substituent or on a    nitrogen by a Z⁷ substituent and may optionally additionally have    further substitution, where the additional substituents on carbon    are each independently selected from Z¹⁻³ and Z⁶, and the additional    substituents on nitrogen are each independently selected from Z² or

-   R¹ is preferably benzofused substituted 5- or 6-membered heteroaryl    which is substituted by one Z⁴ substituent and may additionally    optionally have further substitution, where the additional    substituents on carbon are each independently selected from Z¹⁻²,    and the additional substituents on nitrogen are each independently    selected from Z².

-   R¹ is more preferably phenyl which may contain 1, 2 or 3    substituents, where one substituent is selected from Z⁴ and any    further substituents are selected from the following list: fluorine,    chlorine, bromine, iodine, cyano, nitro, hydroxyl, amino, —SH,    —C(═O)H, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,    1,1-dimethylethyl, 1,2-dimethylethyl, ethenyl, ethynyl,    trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl,    cyclopropyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy,    1,1-dimethylethoxy, methylcarbonyl, ethylcarbonyl,    trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,    n-propoxycarbonyl, 1-methylethoxycarbonyl,    1,1-dimethylethoxycarbonyl, 1-ethenyloxy, 2-propenyloxy,    2-propynyloxy, methylcarbonyloxy, trifluoroalkylcarbonyloxy,    chloromethylcarbonyloxy, methylthio, ethylthio, methylsulphonyl,    methylsulphonylamino, trifluoromethylsulphonylamino or -L³R³, or

-   R¹ is more preferably naphthalen-1-yl, naphthalen-2-yl,    1,2,3,4-tetrahydronaphthalen-1-yl,    1,2,3,4-tetrahydronaphthalen-2-yl,    5,6,7,8-tetrahydronaphthalen-1-yl,    5,6,7,8-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl,    1H-inden-1-yl, 2,3-dihydro-1H-inden-1-yl, 1H-inden-2-yl,    1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl,    1H-inden-7-yl, indan-1-yl, indan-2-yl, indan-3-yl, indan-4-yl or    indan-5-yl, where these may each be substituted at least once by a    Z⁵ substituent and may optionally additionally have further    substitution, where the additional substituents are each    independently selected from Z⁵ and the group consisting of methyl,    methoxy, cyano, fluorine, chlorine, bromine and iodine, where, in    the particularly preferred variant, a total of at most three    substituents are present, or

-   R¹ is more preferably furan-2-yl, furan-3-yl, thiophen-2-yl,    thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl,    pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl,    oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,    isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl,    pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl,    imidazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,    1,3,4-oxadiazol-2-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,    1,3,4-thiadiazol-2-yl, 1,2,3-triazol-1-yl, 1,2,3-triazol-2-yl,    1,2,3-triazol-4-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl,    1,2,4-triazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl,    pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl,    pyrimidin-5-yl or pyrazin-2-yl, each of which may contain 1 or 2    substituent(s), where one substituent is either on a carbon and is    selected from Z⁶ or is on a nitrogen and is selected from Z⁷, and    any further substituent is selected from the following list:    -   substituents on carbon: fluorine, chlorine, bromine, iodine,        cyano, nitro, hydroxyl, methyl, ethyl, n-propyl, 1-methylethyl,        n-butyl, 1,1-dimethylethyl, 1,2-dimethylethyl, ethenyl, ethynyl,        trifluoromethyl, difluoromethyl, trichloromethyl,        dichloromethyl, cyclopropyl, methoxy, ethoxy, n-propoxy,        1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl,        ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl,        ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl,        1,1-dimethylethoxycarbonyl, 1-ethenyloxy, 2-propenyloxy,        2-propinyloxy, methylcarbonyloxy, trifluoroalkylcarbonyloxy,        chloromethylcarbonyloxy, methylcarbonylamino,        trifluoroalkylcarbonyl amino, chloromethylcarbonylamino,        methylthio, ethylthio, methylsulphinyl, methylsulphonyl,        methylsulphonyloxy, trifluoroalkylsulphonyloxy,        methylsulphonylamino or trifluoromethylsulphonylamino,        substituents on nitrogen: methyl, ethyl, n-propyl, —C(═O)H,        methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl,        methylsulphonyl, trifluoromethylsulphonyl, phenylsulphonyl,        phenyl or 2-propynyl, or

-   R¹ is more preferably indol-1-yl, indol-2-yl, indol-3-yl,    indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl,    benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl,    indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl,    indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl,    1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl,    1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl,    1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl,    1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl,    1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl,    1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl,    1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl,    quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl,    quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl,    isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl,    isoquinolin-6-yl, isoquinolin-7-yl or isoquinolin-8-yl, which is    substituted by a substituent, either on a carbon by Z⁶ or on a    nitrogen by Z⁷, and additionally optionally bears a further    substituent selected from the following list:

-   substituents on carbon: fluorine, chlorine, bromine, iodine, methyl,    methoxy,

-   substituents on nitrogen: methyl, ethyl, n-propyl, —C(═O)H,    methylcarbonyl, trifluoromethylcarbonyl, chloromethylcarbonyl,    methylsulphonyl, trifluoromethylsulphonyl, phenylsulphonyl, phenyl    or 2-propynyl,

-   Z¹⁻¹ is hydrogen, halogen, cyano, hydroxyl, nitro, —C(═O)NR³R⁴,    —NR³R⁴, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl,    C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,    C₁-C₆-alkoxycarbonyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₆-alkylcarbonyloxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio,    C₃-C₆-cycloalkylthio or -L³Z³,

-   Z¹⁻² are the same or different and are each independently hydrogen,    halogen, cyano, nitro, —NR³R⁴, —C(═O)NR³R⁴, C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,    C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylcarbonyloxy,    C₁-C₆-alkylcarbonylthio, C₁-C₄-alkylthio or C₁-C₄-haloalkylthio,

-   Z¹⁻³ is hydrogen, halogen, cyano, hydroxyl, nitro, —C(═O)NR³R⁴,    —NR³R⁴, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,    C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl,    C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio or    C₃-C₆-cycloalkylthio,

-   Z² is the same or different and is preferably independently    hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,    C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl, C₁-C₄-haloalkylsulphonyl,    C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl, phenylsulphonyl,    C₁-C₄-alkylsulphonyl, —C(═O)H, C₁-C₃-haloalkylcarbonyl or    C₁-C₃-alkylcarbonyl,

-   L³ is preferably a direct bond, —CH₂—, sulphur, oxygen, and more    preferably a direct bond,

-   Z³ is preferably a phenyl radical, naphthalenyl or a 5- or    6-membered heteroaryl radical which may contain up to two    substituents, where the substituents are each independently selected    from the following list:    -   substituents on carbon: halogen, cyano, nitro, hydroxyl, amino,        —SH, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-haloalkyl,        C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₂-C₄-alkoxyalkyl,        C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl,        C₁-C₆-alkoxycarbonyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,        C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₄-alkylthio,        C₁-C₄-haloalkylthio, C₁-C₄-alkylsulphonyl,        C₁-C₄-haloalkylsulphonyl or C₁-C₄-alkylamino,        di(C₁-C₄-alkyl)amino,    -   substituents on nitrogen: C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,        C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl,        C₁-C₄-haloalkylsulphonyl, C₁-C₆-alkoxycarbonyl,        C₁-C₆-haloalkoxycarbonyl, phenylsulphonyl, C₁-C₄-alkylsulphonyl,        —C(═O)H, or C₁-C₃-alkylcarbonyl, and

-   Z³ is more preferably a phenyl radical which may contain up to two    substituents, where the substituents are each independently selected    from the following list:    -   chlorine, bromine, iodine, fluorine, cyano, nitro, hydroxyl,        amino, —SH, methyl, ethyl, n-propyl, 1-methylethyl,        1,1-dimethylethyl, ethenyl, propen-2-yl, ethynyl, propyn-2-yl,        trifluoromethyl, difluoromethyl, methoxymethyl, methylcarbonyl,        ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl,        ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl,        1,1-dimethylethoxycarbonyl, methoxy, ethoxy, n-propoxy,        1-methylethoxy, 1,1-dimethylethoxy, trifluoromethoxy,        ethenyloxy, 2-propenyloxy, ethynyloxy, 2-propynyloxy,        methylthio, ethylthio, trifluoromethylthio, methylsulphonyl,        ethylsulphonyl, propylthionyl, 1-methylethylthio,        trifluoromethylsulphonyl, methylamino, ethylamino,        n-propylamino, 1-methylethylamino, 1,1-dimethylethylamino or        dimethylamino,

-   Z⁴ is preferably C(═O)H, C₇-C₈-cycloalkyl,    C₃-C₆-cycloalkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,    C₄-C₆-alkoxy-C₁-C₄-alkyl, C₄-C₆-alkoxy-C₁-C₄-alkyl,    C₃-alkoxy-C₂-C₄-alkyl, C₁-C₃-alkoxy-C₂-C₃-alkoxy-C₁-C₃-alkyl,    C₁-C₄-alkylthio-C₁-C₂-alkyl, C₁-C₄-alkylsulphinyl-C₁-C₂-alkyl,    C₁-C₄-alkylsulphonyl-C₁-C₂-alkyl, C₁-C₄-alkylamino-C₁-C₂-alkyl,    C₁-C₂-dialkylamino-C₁-C₂-alkyl, C₁-C₄-haloalkylamino-C₁-C₂-alkyl,    C₃-C₆-cycloalkylamino-C₁-C₂-alkyl, C₄-C₆-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, C₃-C₆-cycloalkylcarbonyl,    C₃-C₆-cycloalkoxycarbonyl, C₃-C₆-cycloalkyl-C₁-C₂-alkoxycarbonyl,    C₃-C₆-cycloalkylaminocarbonyl, C₁-C₄-haloalkoxy-C₁-C₂-alkyl,    C₅-C₆-hydroxyalkyl, C₅-C₆-alkoxy, C₅-C₆-haloalkoxy,    C₃-C₆-cycloalkoxy, C₃-C₆-halocycloalkoxy, C₃-C₆-cycloalkylalkoxy,    C₂-C₆-alkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy,    C₂-C₆-haloalkynyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, cyano-C₁-C₄-alkoxy,    C₁-C₄-haloalkylcarbonyloxy, C₃-C₆-cycloalkylcarbonyloxy,    C₁-C₄-alkylcarbonyl-C₁-C₄-alkoxy, C₅-C₆-alkylthio,    C₅-C₆-haloalkylthio, C₅-C₆-alkylsulphinyl, C₅-C₆-haloalkylsulphinyl,    C₅-C₆-alkylsulphonyl, C₅-C₆-haloalkylsulphonyl,    C₃-C₆-cycloalkylsulphonyl, tri(C₃-C₄-alkyl)silyl,    C₁-C₄-alkylsulphonylamino or C₁-C₄-haloalkylsulphonylamino,

-   Z⁴ is more preferably C(═O)H, cycloheptyl, cyclopropylcyclopropyl,    cyclohexenyl, n-butoxymethyl, n-propoxyethyl, methoxyethoxymethyl,    ethoxyethoxymethyl, methylthiomethyl, ethylthiomethyl,    methylsulphinylmethyl, ethylsulphinylmethyl, methylsulphonylmethyl,    ethylsulphonylmethyl, methylaminomethyl, ethylaminomethyl,    dimethylaminomethyl, trifluoromethylaminomethyl,    cyclopropylaminomethyl, n-butylcarbonyl, n-pentylcarbonyl,    trifluoromethylcarbonyl, cyclopropylcarbonyl, cyclohexylcarbonyl,    cyclopropoxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl,    cyclopropylaminocarbonyl, cyclopentylaminocarbonyl,    cyclohexylaminocarbonyl, difluoromethoxymethyl,    trifluoromethoxymethyl, n-pentoxy, halo-n-pentoxy, cyclopropoxy,    cyclopentyloxy, cyclohexyloxy, cyclopropylmethoxy, allyl,    3-methylbut-2-en-1-yloxy, prop-2-yn-1-yloxy, but-2-yn-1-yloxy,    pent-2-yn-1-yloxy, haloalkynyloxy, methoxyethoxy, methoxypropoxy,    ethoxyethoxy, 3,3,3-trifluoropropanyloxy, cyanomethoxy,    trifluoromethylcarbonyloxy, cyclopropylcarbonyloxy,    cyclopentylcarbonyloxy, cyclohexylcarbonyloxy,    methylcarbonylmethoxy, pentylsulphonyl, methylsulphonylamino,    ethylsulphonylamino or trifluoromethylsulphonylamino,

-   Z⁵ is preferably benzyl, phenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,    C₅-C₆-alkylthio or C₅-C₆-haloalkylthio,

-   Z⁶ is preferably C₃-C₆-cycloalkylcyclopropyl,    C₃-C₆-cycloalkylcyclohexyl or tri(C₃-C₄-alkyl)silyl,

-   Z⁷ is preferably C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl,    C₃-C₆-cycloalkylcyclopropyl, C₃-C₆-cycloalkylcyclohexyl,    cycloalkylalkyl, C₁-C₄-alkylsulphonyl, C(═O)H, benzyl or phenyl.

The heteroarylpiperidine and -piperazine derivatives usable inaccordance with the invention are defined in general terms by theformula (I). The radical definitions of the radical definitions aboveand specified below of the formula (I) apply to the end products of theformula (I), and also equally to all intermediates (see also below under“Elucidations of the processes and intermediates”).

The radical definitions and elucidations listed above and below, ingeneral terms or in areas of preference, can be combined with oneanother as desired, i.e. including combinations between the particularareas and areas of preference. They apply both to the end products andcorrespondingly to precursors and intermediates. Moreover, individualdefinitions may not apply.

Preference is given to those compounds of the formula (I) in which allradicals have the abovementioned preferred definitions.

Particular preference is given to those compounds of the formula (I) inwhich all radicals have the abovementioned more preferred definitions.

Very particular preference is given to those compounds of the formula(I) in which all radicals have the abovementioned most preferreddefinitions.

Preference is additionally given to compounds of the formula (I) andagrochemically active salts, metal complexes and N-oxides thereof, inwhich:

-   A is 5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl,    5-chloro-2-methylphenyl or 2,5-bis(difluoromethyl)phenyl,-   L¹ is —CH₂— or —NH—,-   L² is a direct bond,-   Y is oxygen,-   X is carbon,-   p is 0,-   G is G¹,-   R^(G1) is hydrogen,-   Q is Q²⁴-3,-   R² is hydrogen,-   R⁵ is hydrogen,-   R¹ is 3-formylphenyl, 2-formylphenyl or    2-[(methylsulphonyl)amino]phenyl.

The radical definitions mentioned above can be combined with one anotheras desired. Moreover, individual definitions may not apply.

According to the type of substituents defined above, the compounds ofthe formula (I) have acidic or basic properties and can form salts,possibly also internal salts or adducts, with inorganic or organic acidsor with bases or with metal ions. If the compounds of the formula (I)bear amino, alkylamino or other groups which induce basic properties,these compounds can be reacted with acids to give salts, or they areobtained directly as salts by the synthesis. If the compounds of theformula (I) bear hydroxyl, carboxyl or other groups which induce acidicproperties, these compounds can be reacted with bases to give salts.Suitable bases are, for example, hydroxides, carbonates,hydrogencarbonates of the alkali metals and alkaline earth metals,especially those of sodium, potassium, magnesium and calcium, and alsoammonia, primary, secondary and tertiary amines having C₁-C₄-alkylgroups, mono-, di- and trialkanolamines of C₁-C₄-alkanols, choline andchlorocholine.

The salts thus obtainable likewise have fungicidal properties.

Examples of inorganic acids are hydrohalic acids, such as hydrogenfluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide,sulphuric acid, phosphoric acid and nitric acid, and acidic salts, suchas NaHSO₄ and KHSO₄. Useful organic acids include, for example, formicacid, carbonic acid and alkanoic acids such as acetic acid,trifluoroacetic acid, trichloroacetic acid and propionic acid, and alsoglycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid,benzoic acid, cinnamic acid, oxalic acid, saturated or mono- ordiunsaturated C₆-C₂₀ fatty acids, alkylsulphuric monoesters,alkylsulphonic acids (sulphonic acids having straight-chain or branchedalkyl radicals having 1 to 20 carbon atoms), arylsulphonic acids oraryldisulphonic acids (aromatic radicals, such as phenyl and naphthyl,which bear one or two sulphonic acid groups), alkylphosphonic acids(phosphonic acids having straight-chain or branched alkyl radicalshaving 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonicacids (aromatic radicals, such as phenyl and naphthyl, which bear one ortwo phosphonic acid radicals), where the alkyl and aryl radicals maybear further substituents, for example p-toluenesulphonic acid,salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid,2-acetoxybenzoic acid, etc.

Useful metal ions are especially the ions of the elements of the secondmain group, especially calcium and magnesium, of the third and fourthmain group, especially aluminium, tin and lead, and also of the first toeighth transition groups, especially chromium, manganese, iron, cobalt,nickel, copper, zinc and others. Particular preference is given to themetal ions of the elements of the fourth period. Here, the metals can bepresent in the various valencies that they can assume.

Optionally substituted groups may be mono- or polysubstituted, where thesubstituents in the case of polysubstitutions may be identical ordifferent.

In the definitions of the symbols given in the above formulae,collective terms were used, which are generally representative of thefollowing substituents:

Halogen: fluorine, chlorine, bromine and iodine and preferably fluorine,chlorine, bromine and more preferably fluorine, chlorine.

Alkyl: saturated, straight-chain or branched hydrocarbyl radicals having1 to 8, preferably 1 to 6 and more preferably 1 to 3 carbon atoms, forexample (but not limited to) C₁-C₆-alkyl such as methyl, ethyl, propyl,1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl,pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. This definition alsoapplies to alkyl as part of a composite substituent, for examplecycloalkylalkyl, hydroxyalkyl etc., unless defined elsewhere like, forexample, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl orhaloalkylthio. When the alkyl is at the end of a composite substituent,as, for example, in alkylcycloalkyl, the part of the compositesubstituent at the start, for example the cycloalkyl, may be mono- orpolysubstituted, identically or differently and in each caseindependently, by alkyl. The same also applies to composite substituentsin which other radicals, for example alkenyl, alkynyl, hydroxyl,halogen, formyl, etc. are at the end.

Alkenyl: unsaturated, straight-chain or branched hydrocarbyl radicalshaving 2 to 8, preferably 2 to 6, carbon atoms and one double bond inany position, for example (but not limited to) C₂-C₆-alkenyl such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl. Thisdefinition also applies to alkenyl as part of a composite substituent,for example haloalkenyl etc., unless defined elsewhere.

Alkynyl: straight-chain or branched hydrocarbyl groups having 2 to 8,preferably 2 to 6, carbon atoms and one triple bond in any position, forexample (but not limited to) C₂-C₆-alkynyl, such as ethynyl, 1-propynyl,2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl,1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl,3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl,2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl,4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl,3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl. This definition alsoapplies to alkynyl as part of a composite substituent, for examplehaloalkynyl etc., unless defined elsewhere.

Alkoxy: saturated, straight-chain or branched alkoxy radicals having 1to 8, preferably 1 to 6 and more preferably 1 to 3 carbon atoms, forexample (but not limited to) C1-C6-alkoxy such as methoxy, ethoxy,propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy,1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy,3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy,2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy. This definition also applies to alkoxy aspart of a composite substituent, for example haloalkoxy, alkynylalkoxy,etc., unless defined elsewhere.

Alkylthio: saturated, straight-chain or branched alkylthio radicalshaving 1 to 8, preferably 1 to 6 and more preferably 1 to 3 carbonatoms, for example (but not limited to) C₁-C₆-alkylthio such asmethylthio, ethylthio, propylthio, 1-methylethylthio, butylthio,1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio,pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and1-ethyl-2-methylpropylthio. This definition also applies to alkylthio aspart of a composite substituent, for example haloalkylthio etc., unlessdefined elsewhere.

Alkoxycarbonyl: an alkoxy group which has 1 to 6, preferably 1 to 3,carbon atoms (as specified above) and is bonded to the skeleton via acarbonyl group (—CO—). This definition also applies to alkoxycarbonyl aspart of a composite substituent, for example cycloalkylalkoxycarbonyletc., unless defined elsewhere.

Alkylsulphinyl: saturated, straight-chain or branched alkylsulphinylradicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 3carbon atoms, for example (but not limited to) C₁-C₆-alkylsulphinyl suchas methylsulphinyl, ethylsulphinyl, propylsulphinyl,1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl,2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl,1-methylbutylsulphinyl, 2-methylbutylsulphinyl, 3-methylbutylsulphinyl,2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl,1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl,1-methylpentylsulphinyl, 2-methylpentylsulphinyl,3-methylpentylsulphinyl, 4-methylpentylsulphinyl,1,1-dimethylbutylsulphinyl, 1,2-dimethylbutylsulphinyl,1,3-dimethylbutylsulphinyl, 2,2-dimethylbutylsulphinyl,2,3-dimethylbutylsulphinyl, 3,3-dimethylbutylsulphinyl,1-ethylbutylsulphinyl, 2-ethylbutylsulphinyl,1,1,2-trimethylpropylsulphinyl, 1,2,2-trimethylpropylsulphinyl,1-ethyl-1-methylpropylsulphinyl and 1-ethyl-2-methylpropylsulphinyl.This definition also applies to alkylsulphinyl as part of a compositesubstituent, for example haloalkylsulphinyl etc., unless definedelsewhere.

Alkylsulphonyl: saturated, straight-chain or branched alkylsulphonylradicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 3carbon atoms, for example (but not limited to) C₁-C₆-alkylsulphonyl suchas methylsulphonyl, ethylsulphonyl, propylsulphonyl,1-methylethylsulphonyl, butylsulphonyl, 1-methylpropylsulphonyl,2-methylpropylsulphonyl, 1,1-dimethylethylsulphonyl, pentylsulphonyl,1-methylbutylsulphonyl, 2-methylbutylsulphonyl, 3-methylbutylsulphonyl,2,2-dimethylpropylsulphonyl, 1-ethylpropylsulphonyl, hexylsulphonyl,1,1-dimethylpropylsulphonyl, 1,2-dimethylpropylsulphonyl,1-methylpentylsulphonyl, 2-methylpentylsulphonyl,3-methylpentylsulphonyl, 4-methylpentylsulphonyl,1,1-dimethylbutylsulphonyl, 1,2-dimethylbutylsulphonyl,1,3-dimethylbutylsulphonyl, 2,2-dimethylbutylsulphonyl,2,3-dimethylbutylsulphonyl, 3,3-dimethylbutylsulphonyl,1-ethylbutylsulphonyl, 2-ethylbutylsulphonyl,1,1,2-trimethylpropylsulphonyl, 1,2,2-trimethylpropylsulphonyl,1-ethyl-1-methylpropylsulphonyl and 1-ethyl-2-methylpropylsulphonyl.This definition also applies to alkylsulphonyl as part of a compositesubstituent, for example alkylsulphonylalkyl etc., unless definedelsewhere.

Cycloalkyl: monocyclic, saturated hydrocarbyl groups having 3 to 10,preferably 3 to 8 and more preferably 3 to 6 carbon ring members, forexample (but not limited to) cyclopropyl, cyclopentyl and cyclohexyl.This definition also applies to cycloalkyl as part of a compositesubstituent, for example cycloalkylalkyl etc., unless defined elsewhere.

Cycloalkenyl: monocyclic, partially unsaturated hydrocarbyl groupshaving 3 to 10, preferably 3 to 8 and more preferably 3 to 6 carbon ringmembers, for example (but not limited to) cyclopropenyl, cyclopentenyland cyclohexenyl. This definition also applies to cycloalkenyl as partof a composite substituent, for example cycloalkenylalkyl etc., unlessdefined elsewhere.

Cycloalkoxy: monocyclic, saturated cycloalkyloxy radicals having 3 to10, preferably 3 to 8 and more preferably 3 to 6 carbon ring members,for example (but not limited to) cyclopropyloxy, cyclopentyloxy andcyclohexyloxy. This definition also applies to cycloalkoxy as part of acomposite substituent, for example cycloalkoxyalkyl etc., unless definedelsewhere.

Haloalkyl: straight-chain or branched alkyl groups having 1 to 8,preferably 1 to 6 and more preferably 1 to 3 carbon atoms (as specifiedabove), where some or all of the hydrogen atoms in these groups may bereplaced by halogen atoms as specified above, for example (but notlimited to) C₁-C₃-haloalkyl such as chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl aspart of a composite substituent, for example haloalkylaminoalkyl etc.,unless defined elsewhere.

Haloalkenyl and haloalkynyl are defined analogously to haloalkyl exceptthat, instead of alkyl groups, alkenyl and alkynyl groups are present aspart of the substituent.

Haloalkoxy: straight-chain or branched alkoxy groups having 1 to 8,preferably 1 to 6 and more preferably 1 to 3 carbon atoms (as specifiedabove), where some or all of the hydrogen atoms in these groups may bereplaced by halogen atoms as specified above, for example (but notlimited to) C₁-C₃-haloalkoxy such as chloromethoxy, bromomethoxy,dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy,trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy,2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy,2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxyand 1,1,1-trifluoroprop-2-oxy. This definition also applies tohaloalkoxy as part of a composite substituent, for examplehaloalkoxyalkyl etc., unless defined elsewhere.

Haloalkylthio: straight-chain or branched alkylthio groups having 1 to8, preferably 1 to 6 and more preferably 1 to 3 carbon atoms (asspecified above), where some or all of the hydrogen atoms in thesegroups may be replaced by halogen atoms as specified above, for example(but not limited to) C₁-C₃-haloalkylthio such as chloromethylthio,bromomethylthio, dichloromethylthio, trichloromethylthio,fluoromethylthio, difluoromethylthio, trifluoromethylthio,chlorofluoromethylthio, dichlorofluoromethylthio,chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio,1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio,2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,2,2,2-trichloroethylthio, pentafluoroethylthio and1,1,1-trifluoroprop-2-ylthio. This definition also applies tohaloalkylthio as part of a composite substituent, for examplehaloalkylthioalkyl etc., unless defined elsewhere.

Heteroaryl: 5 or 6-membered, fully unsaturated monocyclic ring systemcontaining one to four heteroatoms from the group of oxygen, nitrogenand sulphur; if the ring contains more than one oxygen atom, they arenot directly adjacent;

-   5-membered heteroaryl containing one to four nitrogen atoms or one    to three nitrogen atoms and one sulphur or oxygen atom: 5-membered    heteroaryl groups which, in addition to carbon atoms, may contain    one to four nitrogen atoms or one to three nitrogen atoms and one    sulphur or oxygen atom as ring members, for example (but not limited    to) 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,    3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,    4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl,    5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,    4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,    1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,    1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl,    1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;-   nitrogen-bonded 5-membered heteroaryl containing one to four    nitrogen atoms, or benzofused nitrogen-bonded 5-membered heteroaryl    containing one to three nitrogen atoms: 5-membered heteroaryl groups    which, in addition to carbon atoms, may contain one to four nitrogen    atoms or one to three nitrogen atoms as ring members and in which    two adjacent carbon ring members or one nitrogen and one adjacent    carbon ring member may be bridged by a buta-1,3-diene-1,4-diyl group    in which one or two carbon atoms may be replaced by nitrogen atoms    in which one or two carbon atoms may be replaced by nitrogen atoms,    where these rings are attached to the skeleton via one of the    nitrogen ring members, for example (but not limited to) 1-pyrrolyl,    1-pyrazolyl, 1,2,4-triazol-1-yl, 1-imidazolyl, 1,2,3-triazol-1-yl    and 1,3,4-triazol-1-yl;-   6-membered heteroaryl which contains one to four nitrogen atoms:    6-membered heteroaryl groups which, in addition to carbon atoms, may    contain, respectively, one to three and one to four nitrogen atoms    as ring members, for example (but not limited to) 2-pyridinyl,    3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,    2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,    1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;-   benzofused 5-membered heteroaryl containing one to three nitrogen    atoms or one nitrogen atom and one oxygen or sulphur atom: for    example (but not limited to) indol-1-yl, indol-2-yl, indol-3-yl,    indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl,    benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl,    indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl,    indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl,    1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl,    1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl,    1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl,    1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl,    1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl,    1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl,    1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl,-   benzofused 6-membered heteroaryl which contains one to three    nitrogen atoms: for example (but not limited to) quinolin-2-yl,    quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl,    quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl,    isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl,    isoquinolin-7-yl and isoquinolin-8-yl.

This definition also applies to heteroaryl as part of a compositesubstituent, for example heteroarylalkyl etc., unless defined elsewhere.

Heterocyclyl: three- to fifteen-membered, preferably three- tonine-membered, saturated or partially unsaturated heterocycle containingone to four heteroatoms from the group of oxygen, nitrogen and sulphur:mono-, bi- or tricyclic heterocycles which contain, in addition tocarbon ring members, one to three nitrogen atoms and/or one oxygen orsulphur atom or one or two oxygen and/or sulphur atoms; if the ringcontains more than one oxygen atom, they are not directly adjacent; forexample (but not limited to) oxiranyl, aziridinyl, 2-tetrahydrofuranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl,4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl,4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl,4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl,4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl,4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl,4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl,1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl. Thisdefinition also applies to heterocyclyl as part of a compositesubstituent, for example heterocyclylalkyl etc., unless definedelsewhere.

Leaving group: S_(N)1 or S_(N)2 leaving group, for example chlorine,bromine, iodine, alkylsulphonates (—OSO₂-alkyl, e.g. —OSO₂CH₃, —OSO₂CF₃)or arylsulphonates (—OSO₂-aryl, e.g. —OSO₂Ph, —OSO₂PhMe).

Not included are combinations which are against natural laws and whichthe person skilled in the art would therefore exclude based on his/herexpert knowledge. Ring structures having three or more adjacent oxygenatoms, for example, are excluded.

Elucidation of the Preparation Processes and Intermediates

The heteroarylpiperidine and -piperazine derivatives of the formula (I)can be prepared in different ways. Initially, the feasable processes areshown schematically below. Unless stated otherwise, the radicals areeach as defined above.

The processes according to the invention for preparing compounds of theformula (I) are optionally performed using one or more reactionauxiliaries.

Useful reaction auxiliaries are, if required, inorganic or organic basesor acid acceptors. These preferably include alkali metal or alkalineearth metal acetates, amides, carbonates, hydrogencarbonates, hydrides,hydroxides or alkoxides, for example sodium acetate, potassium acetateor calcium acetate, lithium amide, sodium amide, potassium amide orcalcium amide, sodium carbonate, potassium carbonate or calciumcarbonate, sodium hydrogencarbonate, potassium hydrogencarbonate orcalcium hydrogencarbonate, lithium hydride, sodium hydride, potassiumhydride or calcium hydride, lithium hydroxide, sodium hydroxide,potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n-or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide,ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; and also basicorganic nitrogen compounds, for example trimethylamine, triethylamine,tripropylamine, tributylamine, ethyldiisopropylamine,N,N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, 2-methyl-,3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and3,5-dimethylpyridine, 5-ethyl-2-methylpyridine, 4-dimethylaminopyridine,N-methylpiperidine, 1,4-diazabicyclo[2.2.2]octane (DABCO),1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The processes according to the invention are optionally performed usingone or more diluents. Useful diluents include virtually all inertorganic solvents. These preferably include aliphatic and aromatic,optionally halogenated hydrocarbons, such as pentane, hexane, heptane,cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene,xylene, methylene chloride, ethylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, ethers such asdiethyl ether and dibutyl ether, glycol dimethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone,methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone,esters, such as methyl acetate and ethyl acetate, nitriles, for exampleacetonitrile and propionitrile, amides, for example dimethylformamide,dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide,tetramethylene sulphone and hexamethylphosphoramide and DMPU.

In the processes according to the invention, the reaction temperaturescan be varied within a relatively wide range. In general, thetemperatures employed are between 0° C. and 250° C., preferablytemperatures between 10° C. and 185° C.

The reaction time varies as a function of the scale of the reaction andof the reaction temperature, but is generally between a few minutes and48 hours.

The processes according to the invention are generally performed understandard pressure. However, it is also possible to work under elevatedor reduced pressure.

For performance of the processes according to the invention, thestarting materials required in each case are generally used inapproximately equimolar amounts. However, it is also possible to use oneof the components used in each case in a relatively large excess.

Process A

W⁹ and W¹⁰ are functional groups suitable for the fomation of thedesired heterocycle and the symbols A, G, Y, X, p, L¹, L², R¹, R² andR¹⁰ are each as defined in the description.

In general, it is possible to prepare compounds of the formula (I) fromcorresponding compounds (XXIII) and (XXIV) with suitable functionalgroups W⁹ and W¹⁰ (I) (see Scheme 1, process A). The possible functionalgroups for W⁹ and W¹⁰ are, for example, aldehydes, ketones, esters,carboxylic acids, amides, thioamides, nitriles, alcohols, thiols,hydrazines, oximes, amidines, amide oximes, olefins, acetylenes,halides, alkyl halides, methanesulphonates, trifluoromethanesulphonates,boronic acids, boronates etc., which can form the desired heterocycle Qunder suitable reaction conditions. There are numerous literaturemethods for the preparation of heterocycles (see WO2008/013622;Comprehensive Heterocyclic Chemistry Vol. 4-6, A. R. Katritzky and C. W.Rees editors, Pergamon Press, New York, 1984; Comprehensive HeterocyclicChemistry II, Vol 2-4, A. R. Katritzky, C. W. Rees and E. F. Scriveneditors, Pergamon Press, New York, 1996; The Chemistry of HeterocyclicCompounds, E. C. Taylor, editor, Wiley, New York; Rodd's Chemistry ofCarbon Compounds, Vol. 2-4, Elsevier, New York; Synthesis, 1982, 6,508-509; Tetrahedron, 2000, 56, 1057-1094; and literature citedtherein).

Process B

The symbols A, G, Y, X, p, L¹, L², R¹, R², R⁵ and R¹⁰ are each asdefined in the description.

A particular means of preparing compounds of the formula (Ie) fromcorresponding compounds (III) by reaction with the compounds (IIa) or(IIb) is shown in Scheme 2.

The alkenes and alkynes (IIa) and (IIb) are commercially available orcan be prepared from commercially available precursors by methodsdescribed in the literature (for example from ketones or aldehydes by aWittig or Horner-Wadsworth-Emmons olefination: Chem. Rev. 1989, 89,863-927 and Julia olefination: Tetrahedron Lett., 1973, 14, 4833-4836;Peterson olefination: J. Org. Chem. 1968, 33, 780; with theBestmann-Ohira reagent: Synthesis 2004, 1, 59-62).

A compound of the general formula (Ie) is obtained from an alkene of thegeneral formula (IIa) or from an alkyne of the formula (IIb) andcompound (III) by a cycloaddition reaction (see, for example, WO08/013622 and Synthesis, 1987, 11, 998-1001).

Process B is performed in the presence of a suitable base. Preferredbases are tertiary amines (e.g. triethylamine), and alkali metal oralkaline earth metal carbonates, hydrogencarbonates and phosphates.

Process B is preferably performed using one or more diluents. In theperformance of process B, inert organic solvents are a preferred option(for example toluene and hexane). Water is likewise a possible solvent.Alternatively, process A can be performed in an excess of the alkene(IIa) or of the alkyne (IIb).

The workup is effected by customary methods. If necessary, the compoundsare purified by recrystallization or chromatography, or can optionallyalso be used in the next step without prior purification.

Process C

The symbols A, G, Y, X, p, L¹, L², R¹, R², R⁵ and R¹⁰ are each asdefined in the description.

One means of preparing the intermediate (III) from compound (IV) isshown in Scheme 3 (process C).

A compound of the general formula (III) is obtained by condensation ofan aldehyde of the formula (IV) with hydroxylamine and subsequentchlorination (see, for example, WO 05/0040159, WO 08/013622 andSynthesis, 1987, 11, 998-1001).

In process C, aldehyde (IV) and hydroxylamine are first reacted (Scheme4, step (a)). The corresponding oxime is subsequently chlorinated in thepresence of a suitable chlorinating agent. Preferred chlorinatingreagents are N-chlorosuccinimide, HClO and chlorine. After step (a) ofprocess C, the reaction mixture can be worked up by customary methods orconverted further directly in step (b).

Process C is preferably performed using one or more diluents. In step(a) of process C according to the invention, preference is given tousing protic solvents, for example ethanol, as the solvent. After theformation of the corresponding oxime from compound (IV), the reactionmixture is diluted in step (b) with a further solvent, for exampletetrahydrofuran, and then aqueous sodium hypochlorite is added. Thechlorination can likewise be effected with the aid ofN-chlorosuccinimide in DMF.

The workup is effected by customary methods. If necessary, the compoundsare purified by recrystallization or chromatography, or can optionallyalso be used in the next step without prior purification.

Process D

W¹¹ and W¹² are functional groups suitable for the fomation of thedesired heterocycle and the symbols A, G, Q, Y, p, L¹, L², R¹, R² andR¹⁰ are each as defined in the description.

In general, it is possible to prepare the intermediate of the formula(I) from corresponding compounds (XXVI) and (XXV) with suitablefunctional groups W¹¹ and W¹², (I) (see Scheme 4, process D). Thepossible functional groups for W¹¹ and W¹² are, for example, aldehydes,ketones, esters, carboxylic acids, amides, thioamides, nitriles,alcohols, thiols, hydrazines, oximes, amidines, amide oximes, olefins,acetylenes, halides, alkyl halides, methanesulphonates,trifluoromethanesulphonates, boric acid, boronates etc. They can formthe desired 5-membered heterocycle G under suitable reaction conditions.There are numerous literature methods for the preparation ofheterocycles (see WO 2008/013622; Comprehensive Heterocyclic ChemistryVol. 4-6, editors: A. R. Katritzky and C. W. Rees, Pergamon Press, NewYork, 1984; Comprehensive Heterocyclic Chemistry II, Vol. 2-4, editors:A. R. Katritzky, C. W. Rees and E. F. Scriven, Pergamon Press, New York,1996; The Chemistry of Heterocyclic Compounds, editor: E. C. Taylor,Wiley, New York; Rodd's Chemistry of Carbon Compounds, Vol. 2-4,Elsevier, New York).

Process E

W² is a leaving group and the symbols A, Y, p, L¹, L², HU 1, R², R⁵ andR¹⁰ are each as defined in the description.

A particular means of synthesizing compounds of the formula (Ie) fromcompounds (IX) with the compounds (VIII) is shown in Scheme 5 (processE).

Thiocarboxamides (IX) are obtainable by methods known from theliterature, for example by thionating the commercially availablecorresponding carboxamide by using, for example, Lawesson's reagent(WO2008/013622, Org. Synth. Vol. 7, 1990, 372).

-Halo ketones or corresponding ketones having a leaving group (e.g.toluenesulphonyloxy ketones) are also obtainable by methods known fromthe literature (for examples see WO2008/013622), (Scheme 6).

W² is a leaving group, W³ is N,N-dimethylamino, N-methoxy-N-methylaminoor morpholin-1-yl and the symbols L², R¹, R² and R⁵ are each as definedin the description.

The thiazoles (Ie) are obtained by a Hantzsch thiazole synthesis fromthe thiocarboxamides (IX) and -halo ketones or corresponding ketoneshaving a leaving group (VIII) (see, for example, “ComprehensiveHeterocyclic Chemistry”, Pergamon Press, 1984; vol. 6, pages 235-363,“Comprehensive Heterocyclic Chemistry II”, Pergamon Press, 1996; vol. 3,pages 373-474 and references cited therein, and WO 07/014290).

Process E is preferably performed using one or more diluents. In theperformance of process E, inert organic solvents are a preferred option(for example N,N-dimethylformamide and ethanol).

If appropriate, an auxiliary base is used, for example triethylamine.

If necessary, the compounds are purified by recrystallization orchromatography, or can optionally also be used in the next step withoutprior purification.

Process F

The symbols A, Q, G, L², p, R¹, R², R^(L22) and R¹⁰ are each as definedin the description.

The amides (Ia) obtained in the performance of process G according tothe invention (Scheme 8) can be converted by means of methods describedin the literature to the corresponding thioamides (Ib) (e.g. Bioorganic& Medicinal Chemistry Letters, 2009, 19(2), 462-468). This involvesreacting the compounds of the formula (Ia) typically with phosphoruspentasulphide or 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane2,4-disulphide (Lawesson's reagent) (see Scheme 7, Process F).

Process F according to the invention is preferably carried out using oneor more diluents. The preferred solvents are toluene, tetrahydrofuranand 1,2-dimethoxyethane.

After the reaction has ended, the compounds (Ib) are separated from thereaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography.

Process G

W⁴=OH or C¹ and the symbols A, Q, G, L², p, R¹, R², R^(L22) and R¹⁰ areeach as defined in the description.

One means of preparing compounds of the formula (Ia) from correspondingcompounds (XIII) with the compounds (IV) is shown in Scheme 8 (processG).

Compounds (IV) are either commercially available or can be prepared byprocesses described in the literature (see, for example, WO 2008/013622and WO 2008/013925).

A compound with the general formula (Ia) can be synthesized analogouslyto methods described in the literature (see, for example WO2007/147336), by a coupling reaction of a compound with thecorresponding general formula (XIII) with a substrate of the generalformula (IV) where W⁴ is chlorine, optionally in the presence of an acidscavenger/base.

At least one equivalent of an acid scavenger/a base (for example Hünig'sbase, triethylamine or commercially available polymeric acid scavengers)is used, in relation to the starting material of the general formula(XIII) If the starting material is a salt, at least two equivalents ofthe acid scavenger are required.

Alternatively, a compound of the formula (Ia) can also be synthesizedfrom the corresponding compound of the formula (XIII) with a substrateof the formula (IV) where W⁴ is hydroxyl in the presence of a couplingreagent, analogously to methods described in the literature (for exampleTetrahedron 2005, 61, 10827-10852, and references cited therein).

Suitable coupling reagents are, for example, peptide coupling reagents(for example N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide mixed with4-dimethylaminopyridine, N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidemixed with 1-hydroxybenzotriazole, bromotripyrrolidinophosphoniumhexafluorophosphate,O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate, etc.).

After the reaction has ended, the compounds (Ia) are separated from thereaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography.

Process H

A¹ is a 5-membered heteroaryl which may contain up to four substituents,where the substituents on carbon are each independently selected fromZ^(A-2) and where the hydrogen in A¹-H is attached via a nitrogen atom,W¹³=leaving group and the symbols A¹, Q, G, L², p, R¹, R², R⁵ and R¹⁰are each as defined in the description.

One means of preparing compounds of the formula (If) from correspondingcompounds (VII) with the compounds (XXVIII) is shown in Scheme 9(process H).

The starting materials (VII) in which W¹³ is a leaving group can beprepared by means of methods described in the literature from compounds(V), (XVIIe) (FIG. 1) or from (XIII) (see, for example, mesylation:Organic Letters, 2003, 2539-2541; tosylation: JP60156601; halogenation:Australian Journal of Chemistry, 1983, 2095-2110). Typically, thecompounds of the formula (VII, W¹³=chlorine) are prepared proceedingfrom an amine of the formula (XIII) and chloroacetyl chloride. Thecompounds (V) in (FIG. 1) are prepared analogously to process G withglycolic acid or hydroxyacetyl chloride from (XIII) (see, for example,WO 2007103187, WO 2006117521, Bioorganic & Medicinal Chemistry Letters,2007, 6326-6329).

The symbols Q, G, L², p, R¹, R², R⁵ and R¹⁰ are each as defined in thedescription.

At least one equivalent of a base (e.g. sodium hydride, potassiumcarbonate) is used in relation to the starting material of the generalformula (XXVIII).

After the reaction has ended, the compounds (If) are separated from thereaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography, or can, if desired, also be used in the next stepwithout prior purification.

Process I

The symbols A, Q, G, Y, L², p, R¹, R², R⁵ and R¹⁰ are each as defined inthe description.

One means of preparing compounds of the formula (Ic) from correspondingcompounds (XIII) with the compounds (XXX) is shown in Scheme 10 (processI).

A compound with the general formula (Ic) can be synthesized analogouslyto methods described in the literature (see, for example WO2009/055514), by a coupling reaction of a compound with thecorresponding general formula (XIII) with a substrate of the generalformula (XXX), optionally in the presence of an acid scavenger/base, forexample triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene or Hünig'sbase.

After the reaction has ended, the compounds (Ic) are separated from thereaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography.

Process J

W⁵ is chlorine or imidazol-1-yl and the symbols A, G, Q, Y, L², p, R¹,R², R^(L11) and R¹⁰ are each as defined in the description.

One means of preparing compounds of the formula (Id) from correspondingcompounds (XVa, see FIG. 2) or (XVb, see FIG. 2) with the compounds(XVI) is shown in Scheme 11 (process J).

FIG. 2

The symbols Q, G, L², p, R¹, R², R⁵ and R¹⁰ are each as defined in thedescription.

The starting materials, carbamoyl and thiocarbamoyl chlorides of theformula (XVa), can be prepared by means of methods described in theliterature from compounds (XIII) (see, for example, Tetrahedron, 2008,7605; Journal of Organic Chemistry, 2004, 3787; Journal of OrganicChemistry, 1983, 4750; European Journal of Organic Chemistry, 2006,1177). Typically, the compounds of the formula (XVa) are preparedproceeding from amines of the formula (XIII) and phosgene, thiophosgeneor the equivalents thereof.

The alternative starting materials, carbamoyl- andthiocarbamoylimidazoles of the formula (XVb), can be prepared by meansof methods described in the literature (see, for example, TetrahedronLetters, 2008, 5279; Tetrahedron, 2005, 7153). Typically, the compoundsof the formula (XVb, W⁵=imidazol-1-yl) are prepared proceeding fromamines of the formula (XIII) and 1,1′-carbonyldiimidazole or1,1′-thiocarbonyldiimidazole.

Process J is optionally performed in the presence of a suitable acidacceptor.

The compounds (Id) obtained in the performance of process J according tothe invention can alternatively in some cases also be obtained withoutusing an acid acceptor, as the corresponding acid chlorides [(Id)-HCl].If required, the compounds (Id) are released by customary methods.

After the reaction has ended, the compounds (Id) are separated from thereaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography.

Process K

W⁶ is acetyl, C₁-C₄-alkoxycarbonyl, benzyl or benzyloxycarbonyl and thesymbols Q, L², p, R¹, R² and R¹⁰ are each as defined in the description.

One means of preparing compounds of the formula (XIII) fromcorresponding compounds (XVII) is shown in Scheme 12 (process K).

A compound of the formula (XVII) is converted to a compound of theformula (XIII) by suitable methods for removing protecting groupsdescribed in the literature (“Protective Groups in Organic Synthesis”;Theodora W. Greene, Peter G. M. Wuts; Wiley-Interscience; Third Edition;1999 494-653).

tert-Butoxycarbonyl and benzyloxycarbonyl protecting groups can beremoved in an acidic medium (for example with hydrochloric acid ortrifluoroacetic acid). Acetyl protecting groups can be removed underbasic conditions (for example with potassium carbonate or caesiumcarbonate). Benzylic protecting groups can be removed hydrogenolyticallywith hydrogen in the presence of a catalyst (for example palladium onactivated carbon).

Acids which can be used for this reaction of deprotectingtert-butoxycarbonyl and benzyloxycarbonyl groups are, for example,trifluoroacetic acid, hydrochloric acid or other acids as described inthe literature (for example “Protective Groups in Organic Synthesis”;Theodora W. Greene, Peter G. M. Wuts; Wiley-Interscience; Third Edition;1999; 494-653).

After the reaction has ended, the compounds (XIII) are separated fromthe reaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography, or can, if desired, also be used in the next stepwithout prior purification. It is also possible to isolate the compoundof the general formula (XIII) as a salt, for example as a salt ofhydrochloric acid or of trifluoroacetic acid.

Process L

W⁶ is acetyl, C₁-C₄-alkoxycarbonyl, benzyl or benzyloxycarbonyl, W¹¹ andW¹² are functional groups suitable for the formation of the desiredheterocycle and the symbols Q, L², p, R¹, R² and R¹⁰ are each as definedin the description.

In general, it is possible to prepare the intermediate (XVII) fromcorresponding compounds (XXII) with compounds (XXV). Process L (Scheme13) is performed analogously to process D (Scheme 4).

Process M

W² is a leaving group, W⁶ is acetyl, C₁-C₄-alkoxycarbonyl, benzyl orbenzyloxycarbonyl and the symbols L², p, R¹, R², R⁵ and R¹⁰ are each asdefined in the description.

Another means of preparing the intermediate of the formula (XVIIa) fromcorresponding compounds (XXI) is shown in Scheme 14 (process M).Compounds (XXI) are either commercially available or can be prepared byprocesses described in the literature (see, for example, WO 2008/013622and WO 2007/014290). Process M is performed analogously to process E(Scheme 5).

Process N

G^(a) is 5-membered heteroaryl; in the compounds of the formula (XVIIb),the 5-membered heteroaryl is bonded via a nitrogen atom to thepiperidine radical, W⁶ is acetyl, C₁-C₄- alkoxycarbonyl, benzyl orbenzyloxycarbonyl, W⁷ is a leaving group and the symbols Q, L², p, R¹,R² and R¹⁰ are each as defined in the description.

A compound with the general formula (XVIIb) can be synthesizedanalogously to methods described in the literature by a couplingreaction of a compound with the corresponding general formula (XX) witha substrate of the general formula (XIX), optionally in the presence ofa base (Scheme 15, process N). (See, for example, for Zn/Pd coupling: WO2008/147831, WO 2006/106423 (pyridine), Shakespeare, W. C. et al Chem.Biol. Drug Design 2008, 71, 97-105 (pyrimidine derivatives), Pasternak,A. et al Bioorg. Med. Chem. Lett. 2008, 18, 994-998 (diazines);Coleridge, B. M.; Bello, C. S.; Leitner, A. Tetrahedron Lett. 2009, 50,4475-4477; Bach, T., Heuser, S. Angew. Chem. Int. Ed. 2001, 40,3184-3185. (thiazoles); for nucleophilic substitutions: WO 2008/104077;WO 2006/084015 (pyrazoles with N-substitution).)

At least one equivalent of a base (e.g. sodium hydride, potassiumcarbonate) is used in relation to the starting material of the generalformula (XX).

After the reaction has ended, the compounds (XVIIb) are separated fromthe reaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography, or can, if desired, also be used in the next stepwithout prior purification.

Process O

G^(b) is 5-membered heteroaryl; in the compounds of the formula (XVIIc),the 5-membered heteroaryl is bonded via a carbon atom to the piperazinering, W⁶ is acetyl, C₁-C₄- alkoxycarbonyl, benzyl or benzyloxycarbonyl,W⁸ is a leaving group and the symbols Q, L², p, R¹, R² and R¹⁰ are eachas defined in the description.

A compound having the general formula (XVIIc) can be synthesizedanalogously to methods described in the literature (see, for example,for nucleophilic substitutions: Li, C. S., Belair, L., Guay, J. et alBioorg. Med. Chem. Lett. 2009, 19, 5214-5217; WO 2008/062276; for coppercouplings: Yeh, V. S. C.; Wiedeman, P. E. Tetrahedron Lett. 2006, 47,6011-6016; for palladium couplings: WO 2008/157500) by a couplingreaction of a compound having the corresponding general formula (XXIX)with a substrate of the general formula (XIV), optionally in thepresence of a base (Scheme 16, process O).

At least one equivalent of a base (e.g. sodium hydride, potassiumcarbonate) is used in relation to the starting material of the generalformula (XXIX).

After the reaction has ended, the compounds (XVIIc) are separated fromthe reaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography, or can, if desired, also be used in the next stepwithout prior purification.

Process P

W⁶ is acetyl, C₁-C₄-alkoxycarbonyl, benzyl or benzyloxycarbonyl, W⁹ andW¹⁰ are functional groups suitable for the formation of the desiredheterocycle and the symbols Q, L², G, p, R¹, R² and R¹⁰ are each asdefined in the description.

In general, it is possible to prepare the intermediate (XVII) fromcorresponding compounds (XXVII) and (XXIII) Process P (Scheme 17) isperformed analogously to process A (Scheme 1).

Process Q

W⁶ is acetyl, C₁-C₄-alkoxycarbonyl, benzyl or benzyloxycarbonyl and thesymbols X L², G, p, R¹, R², R⁵ and R¹⁰ are each as defined in thedescription.

A particular means of preparing the intermediate (XVIId) fromcorresponding compounds (XVIII) is shown in Scheme 18 (process Q). Thestarting materials of the formula (XVIII) can be prepared by means ofmethods described in the literature (see, for example, WO 2008/013622),and process Q is performed analogously to process B (Scheme 2).

The invention further provides for the non-medical use of the inventiveheteroarylpiperidine and -piperazine derivatives of the formula (I) forcontrol of unwanted microorganisms.

Novel compounds are those of the formula (VII)

and salts, metal complexes and N-oxides thereof, in which the symbolsR², X, G, Q, L², R¹, R¹⁰ and p each have the above-specified general,preferred, more preferred or most preferred definitions and W¹³ is aleaving group.

Novel compounds are those of the formula (XVIId)

for example (XVIII)

and salts, metal complexes and N-oxides thereof, in which the symbol W⁶is acetyl, C₁-C₄-alkoxycarbonyl, benzyl or benzyloxycarbonyl and the X,L², p, R¹, R², R⁵ and R¹⁰ radicals each have the above-specifiedgeneral, preferred, more preferred or most preferred definitions.

Novel compounds are those of the formula (XIIIa)

for example (XIIIb)

and salts, metal complexes and N-oxides thereof, in which the symbols X,L², p, G, R¹, R², R⁵ and R¹⁰ have the above-specified general,preferred, more preferred or most preferred definitions.

The invention further provides a composition for controlling unwantedmicroorganisms, comprising at least one heteroarylpiperidine and-piperazine derivative according to the present invention.

The invention also relates to a method for controlling unwantedmicroorganisms, characterized in that the inventive heteroarylpiperidineand -piperazine derivatives are applied to the microorganisms and/or intheir habitat.

The invention further relates to seed which has been treated with atleast one inventive heteroarylpiperidine and -piperazine derivative.

The invention finally provides a method for protecting seed againstunwanted microorganisms by using seed treated with at least oneheteroarylpiperidine and -piperazine derivative according to the presentinvention.

The inventive substances have potent microbicidal activity and can beused for control of unwanted microorganisms, such as fungi and bacteria,in crop protection and in the protection of materials.

The inventive heteroarylpiperidine and -piperazine derivatives of theformula (I) have very good fungicidal properties and can be used in cropprotection, for example for control of Plasmodiophoromycetes, Oomycetes,Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes andDeuteromycetes.

Bactericides can be employed in crop protection, for example, forcontrolling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae,Corynebacteriaceae and Streptomycetaceae.

The inventive fungicidal compositions can be used for curative orprotective control of phytopathogenic fungi. The invention thereforealso relates to curative and protective methods for controllingphytopathogenic fungi by the use of the inventive active ingredients orcompositions, which are applied to the seed, the plant or plant parts,the fruit or the soil in which the plants grow.

The inventive compositions for controlling phytopathogenic fungi in cropprotection comprise an effective but non-phytotoxic amount of theinventive active ingredients. An “effective but non-phytotoxic amount”means an amount of the inventive composition which is sufficient tocontrol the fungal disease of the plant in a satisfactory manner or toeradicate the fungal disease completely, and which, at the same time,does not cause any significant symptoms of phytotoxicity. In general,this application rate may vary within a relatively wide range. Itdepends on several factors, for example on the fungus to be controlled,the plant, the climatic conditions and the ingredients of the inventivecompositions.

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and plantpopulations, such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants may be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant cultivars which are protectable and non-protectable by plantbreeders' rights. Plant parts are understood to mean all parts andorgans of plants above and below the ground, such as shoot, leaf, flowerand root, examples of which include leaves, needles, stalks, stems,flowers, fruit bodies, fruits and seeds, and also roots, tubers andrhizomes. The plant parts also include harvested material and vegetativeand generative propagation material, for example cuttings, tubers,rhizomes, slips and seeds.

Plants which can be treated in accordance with the invention include thefollowing: cotton, flax, grapevine, fruit, vegetables, such as Rosaceaesp. (for example pome fruits such as apples and pears, but also stonefruits such as apricots, cherries, almonds and peaches, and soft fruitssuch as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceaesp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana treesand plantations), Rubiaceae sp. (for example coffee), Theaceae sp.,Sterculiceae sp., Rutaceae sp. (for example lemons, oranges andgrapefruit); Solanaceae sp. (for example tomatoes), Liliaceae sp.,Asteraceae sp. (for example lettuce), Umbelhferae sp., Cruciferae sp.,Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceaesp. (for example leek, onion), Papilionaceae sp. (for example peas);major crop plants, such as Gramineae sp. (for example maize, turf,cereals such as wheat, rye, rice, barley, oats, millet and triticale),Asteraceae sp. (for example sunflower), Brassicaceae sp. (for examplewhite cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pakchoi, kohlrabi, radishes, and oilseed rape, mustard, horseradish andcress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (forexample soya bean), Solanaceae sp. (for example potatoes),Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard,beetroot); useful plants and ornamental plants in gardens and woods; andgenetically modified varieties of each of these plants.

Non-limiting examples of pathogens of fungal diseases which can betreated in accordance with the invention include:

diseases caused by powdery mildew pathogens, for example Blumeriaspecies, for example Blumeria graminis; Podosphaera species, for examplePodosphaera leucotricha; Sphaerotheca species, for example Sphaerothecafuliginea; Uncinula species, for example Uncinula necator;diseases caused by rust disease pathogens, for example Gymnosporangiumspecies, for example Gymnosporangium sabinae; Hemileia species, forexample Hemileia vastatrix; Phakopsora species, for example Phakopsorapachyrhizi or Phakopsora meibomiae; Puccinia species, for examplePuccinia recondita, Puccinia graminis or Puccinia striiformis; Uromycesspecies, for example Uromyces appendiculatus;diseases caused by pathogens from the group of the Oomycetes, forexample Albugo species, for example Albugo candida; Bremia species, forexample Bremia lactucae; Peronospora species, for example Peronosporapisi or P. brassicae; Phytophthora species, for example Phytophthorainfestans; Plasmopara species, for example Plasmopara viticola;Pseudoperonospora species, for example Pseudoperonospora humuli orPseudoperonospora cubensis; Pythium species, for example Pythiumultimum;leaf blotch diseases and leaf wilt diseases caused, for example, byAlternaria species, for example Alternaria solani; Cercospora species,for example Cercospora beticola; Cladosporium species, for exampleCladosporium cucumerinum; Cochliobolus species, for example Cochliobolussativus (conidial form: Drechslera, syn: Helminthosporium) orCochliobolus miyabeanus; Colletotrichum species, for exampleColletotrichum lindemuthanium; Cycloconium species, for exampleCycloconium oleaginum; Diaporthe species, for example Diaporthe citri;Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species,for example Gloeosporium laeticolor; Glomerella species, for exampleGlomerella cingulata; Guignardia species, for example Guignardiabidwelli; Leptosphaeria species, for example Leptosphaeria maculans;Magnaporthe species, for example Magnaporthe grisea; Microdochiumspecies, for example Microdochium nivale; Mycosphaerella species, forexample Mycosphaerella graminicola, Mycosphaerella arachidicola orMycosphaerella fijiensis; Phaeosphaeria species, for examplePhaeosphaeria nodorum; Pyrenophora species, for example Pyrenophorateres or Pyrenophora tritici repentis; Ramularia species, for exampleRamularia collo-cygni or Ramularia areola; Rhynchosporium species, forexample Rhynchosporium secalis; Septoria species, for example Septoriaapii or Septoria lycopersici; Stagonospora species, for exampleStagonospora nodorum; Typhula species, for example Typhula incarnata;Venturia species, for example Venturia inaequalis;root and stem diseases caused, for example, by Corticium species, forexample Corticium graminearum; Fusarium species, for example Fusariumoxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis;Plasmodiophora species, for example Plasmodiophora brassicae;Rhizoctonia species, for example Rhizoctonia solani; Sarocladiumspecies, for example Sarocladium oryzae; Sclerotium species, for exampleSclerotium oryzae; Tapesia species, for example Tapesia acuformis;Thielaviopsis species, for example Thielaviopsis basicola;ear and panicle diseases (including maize cobs) caused, for example, byAlternaria species, for example Alternaria spp.; Aspergillus species,for example Aspergillus flavus; Cladosporium species, for exampleCladosporium cladosporioides; Claviceps species, for example Clavicepspurpurea; Fusarium species, for example Fusarium culmorum; Gibberellaspecies, for example Gibberella zeae; Monographella species, for exampleMonographella nivalis; Stagnospora species, for example Stagnosporanodorum;diseases caused by smut fungi, for example Sphacelotheca species, forexample Sphacelotheca reiliana; Tilletia species, for example Tilletiacaries or Tilletia controversa; Urocystis species, for example Urocystisocculta; Ustilago species, for example Ustilago nuda;fruit rot caused, for example, by Aspergillus species, for exampleAspergillus flavus; Botrytis species, for example Botrytis cinerea;Penicillium species, for example Penicillium expansum or Penicilliumpurpurogenum; Rhizopus species, for example Rhizopus stolonifer;Sclerotinia species, for example Sclerotinia sclerotiorum; Verticiliumspecies, for example Verticilium alboatrum;seed- and soil-borne rot and wilt diseases, and also diseases ofseedlings, caused, for example, by Alternaria species, for exampleAlternaria brassicicola; Aphanomyces species, for example Aphanomyceseuteiches; Ascochyta species, for example Ascochyta lentis; Aspergillusspecies, for example Aspergillus flavus; Cladosporium species, forexample Cladosporium herbarum; Cochliobolus species, for exampleCochliobolus sativus (conidial form: Drechslera, Bipolaris syn:Helminthosporium); Colletotrichum species, for example Colletotrichumcoccodes; Fusarium species, for example Fusarium culmorum; Gibberellaspecies, for example Gibberella zeae; Macrophomina species, for exampleMacrophomina phaseolina; Microdochium species, for example Microdochiumnivale; Monographella species, for example Monographella nivalis;Penicillium species, for example Penicillium expansum; Phoma species,for example Phoma lingam; Phomopsis species, for example Phomopsissojae; Phytophthora species, for example Phytophthora cactorum;Pyrenophora species, for example Pyrenophora graminea; Pyriculariaspecies, for example Pyricularia oryzae; Pythium species, for examplePythium ultimum; Rhizoctonia species, for example Rhizoctonia solani;Rhizopus species, for example Rhizopus oryzae; Sclerotium species, forexample Sclerotium rolfsii; Septoria species, for example Septorianodorum; Typhula species, for example Typhula incarnata; Verticilliumspecies, for example Verticillium dahliae;cancers, galls and witches' broom caused, for example, by Nectriaspecies, for example Nectria galligena;wilt diseases caused, for example, by Monilinia species, for exampleMonilinia laxa;deformations of leaves, flowers and fruits caused, for example, byExobasidium species, for example Exobasidium vexans; Taphrina species,for example Taphrina deformans;degenerative diseases in woody plants, caused, for example, by Escaspecies, for example Phaeomoniella chlamydospora, Phaeoacremoniumaleophilum or Fomitiporia mediterranea; Ganoderma species, for exampleGanoderma boninense;diseases of flowers and seeds caused, for example, by Botrytis species,for example Botrytis cinerea;diseases of plant tubers caused, for example, by Rhizoctonia species,for example Rhizoctonia solani; Helminthosporium species, for exampleHelminthosporium solani;diseases caused by bacterial pathogens, for example Xanthomonas species,for example Xanthomonas campestris pv. oryzae; Pseudomonas species, forexample Pseudomonas syringae pv. lachrymans; Erwinia species, forexample Erwinia amylovora.

The following diseases of soya beans can be controlled with preference:

Fungal diseases on leaves, stems, pods and seeds caused, for example, byAlternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose(Colletotrichum gloeosporoides dematium var. truncatum), brown spot(Septoria glycines), cercospora leaf spot and blight (Cercosporakikuchii), choanephora leaf blight (Choanephora infundibulifera trispora(Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew(Peronospora manshurica), drechslera blight (Drechslera glycini),frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot(Leptosphaerulina trifolii), phyllostica leaf spot (Phyllostictasojaecola), pod and stem blight (Phomopsis sojae), powdery mildew(Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines),rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust(Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphacelomaglycines), stemphylium leaf blight (Stemphylium botryosum), target spot(Corynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by blackroot rot (Calonectria crotalariae), charcoal rot (Macrophominaphaseolina), fusarium blight or wilt, root rot, and pod and collar rot(Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusariumequiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris),neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthephaseolorum), stem canker (Diaporthe phaseolorum var. caulivora),phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophoragregata), pythium rot (Pythium aphanidermatum, Pythium irregulare,Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctoniaroot rot, stem decay, and damping-off (Rhizoctonia solani), sclerotiniastem decay (Sclerotinia sclerotiorum), sclerotinia southern blight(Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

The inventive active ingredients also have very good fortifying actionin plants. They can therefore be used to mobilize the plant's owndefences against attack by unwanted microorganisms.

Plant-fortifying (resistance-inducing) substances are understood tomean, in the present context, those substances which are capable ofstimulating the defence system of plants in such a way that the treatedplants, when subsequently inoculated with unwanted microorganisms,develop a high degree of resistance to these microorganisms.

In the present case, unwanted microorganisms are understood to meanphytopathogenic fungi and bacteria. The inventive substances can thus beused to protect plants for a certain period after the treatment againstattack by the pathogens mentioned. The period for which protection isprovided generally extends over 1 to 10 days, preferably 1 to 7 days,after the treatment of the plants with the active ingredients.

The fact that the active ingredients are well tolerated by plants at theconcentrations required for controlling plant diseases allows thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The inventive active ingredients can be used particularly successfullyto control diseases in viticulture and potato, fruit and vegetablegrowing, for example especially against powdery mildew fungi, Oomycetes,for example Phytophthora, Plasmopara, Pseudoperonospora and Pythiumspecies.

The inventive active ingredients are also suitable for enhancing theyield of crops. In addition, they have low toxicity and are welltolerated by plants.

If appropriate, the inventive compounds can, at certain concentrationsor application rates, also be used as herbicides, safeners, growthregulators or agents to improve plant properties, or as microbicides,for example as fungicides, antimycotics, bactericides, viricides(including agents against viroids) or as agents against MLO(mycoplasma-like organisms) and RLO (rickettsia-like organisms). Ifappropriate, they can also be used as insecticides. If appropriate, theycan also be used as intermediates or precursors for the synthesis ofother active ingredients.

The inventive active ingredients, when they are well tolerated byplants, have favourable homeotherm toxicity and are well tolerated bythe environment, are suitable for protecting plants and plant organs,for enhancing harvest yields, for improving the quality of the harvestedmaterial in agriculture, in horticulture, in animal husbandry, inforests, in gardens and leisure facilities, in the protection of storedproducts and of materials, and in the hygiene sector. They canpreferably be used as crop protection agents. They are effective againstnormally sensitive and resistant species and against all or some stagesof development.

The inventive treatment of the plants and plant parts with the activeingredients or compositions is effected directly or by action on theirsurroundings, habitat or storage space by the customary treatmentmethods, for example by dipping, spraying, atomizing, irrigating,evaporating, dusting, fogging, broadcasting, foaming, painting,spreading-on, watering (drenching), drip irrigating and, in the case ofpropagation material, especially in the case of seeds, also by dry seedtreatment, wet seed treatment, slurry treatment, incrustation, coatingwith one or more coats, etc. It is also possible to deploy the activeingredients by the ultra-low volume method or to inject the activeingredient preparation/the active ingredient itself into the soil.

The inventive active ingredients or compositions can also be used in theprotection of materials, for protecting industrial materials againstattack and destruction by unwanted microorganisms, for example fungi.

Industrial materials in the present context are understood to meaninanimate materials which have been prepared for use in industry. Forexample, industrial materials which are to be protected by inventiveactive ingredients from microbial alteration or destruction may beadhesives, sizes, paper and board, textiles, leather, wood, paints andplastic articles, cooling lubricants and other materials which can beinfected with or destroyed by microorganisms. The range of materials tobe protected also includes parts of production plants, for examplecooling water circuits, which may be impaired by the proliferation ofmicroorganisms. Industrial materials within the scope of the presentinvention preferably include adhesives, sizes, paper and cardboard,leather, wood, paints, cooling lubricants and heat transfer fluids, morepreferably wood. The inventive active ingredients or compositions mayprevent adverse effects, such as rotting, decay, discoloration,decoloration or formation of mould.

The inventive method for controlling unwanted fungi can also be employedfor protecting storage goods. Storage goods are understood to meannatural substances of vegetable or animal origin or processed productsthereof which are of natural origin, and for which long-term protectionis desired. Storage goods of vegetable origin, for example plants orplant parts, such as stems, leaves, tubers, seeds, fruits, grains, canbe protected freshly harvested or after processing by (pre)drying,moistening, comminuting, grinding, pressing or roasting. Storage goodsalso include timber, whether unprocessed, such as construction timber,electricity poles and barriers, or in the form of finished products,such as furniture. Storage goods of animal origin are, for example,hides, leather, furs and hairs. The inventive active ingredients mayprevent adverse effects, such as rotting, decay, discoloration,decoloration or formation of mould.

Microorganisms capable of degrading or altering the industrial materialsinclude, for example, bacteria, fungi, yeasts, algae and slimeorganisms. The inventive active ingredients preferably act againstfungi, especially moulds, wood-discoloring and wood-destroying fungi(Basidiomycetes), and against slime organisms and algae. Examplesinclude microorganisms of the following genera: Alternaria, such asAlternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium,such as Chaetomium globosum; Coniophora, such as Coniophora puetana;Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicilliumglaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such asAureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila;Trichoderma, such as Trichoderma viride; Escherichia, such asEscherichia coli; Pseudomonas, such as Pseudomonas aeruginosa;Staphylococcus, such as Staphylococcus aureus.

The present invention further relates to a composition for controllingunwanted microorganisms, comprising at least one of the inventiveheteroarylpiperidine and -piperazine derivatives. These are preferablyfungicidal compositions which comprise agriculturally suitableauxiliaries, solvents, carriers, surfactants or extenders.

According to the invention, a carrier is a natural or synthetic, organicor inorganic substance with which the active ingredients are mixed orcombined for better applicability, in particular for application toplants or plant parts or seed. The carrier, which may be solid orliquid, is generally inert and should be suitable for use inagriculture.

Useful solid carriers include: for example ammonium salts and naturalrock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite,montmorillonite or diatomaceous earth, and synthetic rock flours, suchas finely divided silica, alumina and silicates; useful solid carriersfor granules include: for example, crushed and fractionated naturalrocks such as calcite, marble, pumice, sepiolite and dolomite, and alsosynthetic granules of inorganic and organic flours, and granules oforganic material such as paper, sawdust, coconut shells, maize cobs andtobacco stalks; useful emulsifiers and/or foam-formers include: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; suitable dispersants are nonionic and/orionic substances, for example from the classes of the alcohol-POE and/or-POP ethers, acid and/or POP POE esters, alkylaryl and/or POP POEethers, fat and/or POP POE adducts, POE- and/or POP-polyol derivatives,POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates,alkyl- or arylsulphonates and alkyl or aryl phosphates or thecorresponding PO-ether adducts. Additionally suitable are oligo- orpolymers, for example those derived from vinylic monomers, from acrylicacid, from EO and/or PO alone or in combination with, for example,(poly)alcohols or (poly)amines. It is also possible to use lignin andits sulphonic acid derivatives, unmodified and modified celluloses,aromatic and/or aliphatic sulphonic acids and also their adducts withformaldehyde.

The active ingredients can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspoemulsion concentrates, natural productsimpregnated with active ingredient, synthetic substances impregnatedwith active ingredient, fertilizers and also microencapsulations inpolymeric substances.

The active ingredients can be applied as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsions, water- or oil-based suspensions, powders, wettablepowders, pastes, soluble powders, dusts, soluble granules, granules forbroadcasting, suspoemulsion concentrates, natural products impregnatedwith active ingredient, synthetic substances impregnated with activeingredient, fertilizers and also microencapsulations in polymericsubstances. Application is accomplished in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is also possible to apply the activeingredients by the ultra-low volume method, or to inject the activeingredient preparation or the active ingredient itself into the soil. Itis also possible to treat the seed of the plants.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active ingredients with at least one customaryextender, solvent or diluent, emulsifier, dispersant and/or binder orfixing agent, wetting agent, a water repellent, if appropriatesiccatives and UV stabilizers and if appropriate dyes and pigments,antifoams, preservatives, secondary thickeners, stickers, gibberellinsand also other processing auxiliaries.

The present invention includes not only formulations which are alreadyready for use and can be deployed with a suitable apparatus to the plantor the seed, but also commercial concentrates which have to be dilutedwith water prior to use.

The inventive active ingredients may be present as such or in their(commercial) formulations and in the use forms prepared from theseformulations as a mixture with other (known) active ingredients, such asinsecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth regulators, herbicides, fertilizers,safeners and/or semiochemicals.

The auxiliaries used may be those substances which are suitable forimparting particular properties to the composition itself or and/or topreparations derived therefrom (for example spray liquors, seeddressings), such as certain technical properties and/or also particularbiological properties. Typical auxiliaries include: extenders, solventsand carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnonaromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which mayoptionally also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

Liquefied gaseous extenders or carriers are understood to mean liquidswhich are gaseous at standard temperature and under standard pressure,for example aerosol propellants such as halohydrocarbons, or elsebutane, propane, nitrogen and carbon dioxide.

In the formulations it is possible to use tackifiers such ascarboxymethylcellulose, natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further additives may be mineraland vegetable oils.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Useful liquid solvents areessentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, alcohols such as butanol or glycol and their ethers andesters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, or else water.

The inventive compositions may additionally comprise further components,for example surfactants. Suitable surfactants are emulsifiers and/orfoam formers, dispersants or wetting agents having ionic or nonionicproperties, or mixtures of these surfactants. Examples thereof are saltsof polyacrylic acid, salts of lignosulphonic acid, salts ofphenolsulphonic acid or naphthalenesulphonic acid, polycondensates ofethylene oxide with fatty alcohols or with fatty acids or with fattyamines, substituted phenols (preferably alkylphenols or arylphenols),salts of sulphosuccinic esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols,fatty esters of polyols, and derivatives of the compounds containingsulphates, sulphonates and phosphates, for example alkylaryl polyglycolethers, alkylsulphonates, alkyl sulphates, arylsulphonates, proteinhydrolysates, lignosulphite waste liquors and methylcellulose. Thepresence of a surfactant is necessary if one of the active ingredientsand/or one of the inert carriers is insoluble in water and whenapplication is effected in water. The proportion of surfactants isbetween 5 and 40 per cent by weight of the inventive composition.

It is possible to use dyes such as inorganic pigments, for example ironoxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

Further additives may be perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers,preservatives, antioxidants, light stabilizers, or other agents whichimprove chemical and/or physical stability.

If appropriate, it is also possible for other additional components tobe present, for example protective colloids, binders, adhesives,thickeners, thixotropic substances, penetrants, stabilizers,sequestrants, complexing agents. In general, the active ingredients canbe combined with any solid or liquid additive commonly used forformulation purposes.

The formulations contain generally between 0.05 and 99% by weight, 0.01and 98% by weight, preferably between 0.1 and 95% by weight, morepreferably between 0.5 and 90% of active ingredient, most preferablybetween 10 and 70 per cent by weight.

The formulations described above can be used in an inventive method forcontrolling unwanted microorganisms, in which the inventiveheteroarylpiperidine and -piperazine derivatives are applied to themicroorganisms and/or in their habitat.

The inventive active ingredients can also be used, as such or informulations thereof, in a mixture with known fungicides, bactericides,acaricides, nematicides or insecticides, in order thus to broaden, forexample, the activity spectrum or to prevent development of resistance.

Useful mixing partners include, for example, known fungicides,insecticides, acaricides, nematicides or else bactericides (see alsoPesticide Manual, 14th ed.).

A mixture with other known active ingredients, such as herbicides, orwith fertilizers and growth regulators, safeners and/or semiochemicalsis also possible.

Application is accomplished in a customary manner appropriate for theuse forms.

The invention further comprises a method for treating seed.

A further aspect of the present invention relates in particular to seedtreated with at least one of the inventive heteroarylpiperidine and-piperazine derivatives. The inventive seeds are used in methods forprotection of seed from phytopathogenic harmful fungi. In these methods,seed treated with at least one inventive active ingredient is used.

The inventive active ingredients or compositions are also suitable forthe treatment of seed. A large part of the damage to crop plants causedby harmful organisms is triggered by the infection of the seed duringstorage or after sowing both during and after germination of the plant.This phase is particularly critical since the roots and shoots of thegrowing plant are particularly sensitive, and even small damage mayresult in the death of the plant. Accordingly, there is great interestin protecting the seed and the germinating plant by using appropriatecompositions.

The control of phytopathogenic harmful fungi by treating the seed ofplants has been known for a long time and is the subject of constantimprovements. However, the treatment of seed entails a series ofproblems which cannot always be solved in a satisfactory manner. Forinstance, it is desirable to develop methods for protecting the seed andthe germinating plant, which dispense with, or at least significantlyreduce, the additional deployment of crop protection agents afterplanting or after emergence of the plants. It is also desirable tooptimize the amount of the active ingredient used so as to provide thebest possible protection for the seed and the germinating plant fromattack by phytopathogenic fungi, but without damaging the plant itselfby the active ingredient used. In particular, methods for the treatmentof seed should also take account of the intrinsic fungicidal propertiesof transgenic plants in order to achieve optimal protection of the seedand the germinating plant with a minimum expenditure of crop protectionagents.

The present invention therefore also relates to a method for protectingseed and germinating plants against attack by animal pests and/orphytopathogenic harmful fungi by treating the seed with an inventivecomposition. The invention also relates to the use of the inventivecompositions for treatment of seed for protection of the seed and thegerminating plant against phytopathogenic fungi. The invention furtherrelates to seed which has been treated with an inventive composition forprotection from phytopathogenic fungi.

Animal pests and/or phytopathogenic harmful fungi which damage plantspost-emergence are controlled primarily by the treatment of the soil andof the exposed parts of plants with crop protection agents. Owing to theconcerns regarding a possible influence of the crop protection agents onthe environment and the health of humans and animals, there are effortsto reduce the amount of active ingredients deployed.

One of the advantages of the present invention is that, because of theparticular systemic properties of the inventive compositions, thetreatment of the seed with these compositions not only protects the seeditself, but also the resulting plants after emergence, from animal pestsand/or phytopathogenic harmful fungi. In this way, the immediatetreatment of the crop at the time of sowing or shortly thereafter can bedispensed with.

It is likewise considered to be advantageous that the inventive activeingredients or compositions can be used especially also for transgenicseed, in which case the plant which grows from this seed is capable ofexpressing a protein which acts against pests. The treatment of suchseed with the inventive active ingredients or compositions, merelythrough the expression of the protein, for example an insecticidalprotein, can result in control of certain pests. Surprisingly, a furthersynergistic effect can be observed in this case, which additionallyincreases the effectiveness for protection against attack by pests.

The inventive compositions are suitable for protection of seed of anyplant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, the seed is that ofcereals (such as wheat, barley, rye, millet and oats), maize, cotton,soya, rice, potatoes, sunflower, bean, coffee, beet (e.g. sugar beet andfodder beet), peanut, vegetables (such as tomato, cucumber, onions andlettuce), lawns and ornamental plants. Of particular significance is thetreatment of the seed of cereals (such as wheat, barley, rye and oats),maize and rice.

As also described below, the treatment of transgenic seed with theinventive active ingredients or compositions is of particularsignificance. This refers to the seed of plants containing at least oneheterologous gene which allows the expression of a polypeptide orprotein having insecticidal properties. The heterologous gene intransgenic seed may originate, for example, from microorganisms of thespecies Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. This heterologous gene preferablyoriginates from Bacillus sp., in which case the gene product iseffective against the European corn borer and/or the Western cornrootworm. The heterologous gene more preferably originates from Bacillusthuringiensis.

In the context of the present invention, the inventive composition isapplied to the seed either alone or in a suitable formulation.Preferably, the seed is treated in a state in which it is sufficientlystable for no damage to occur in the course of treatment. In general,the seed can be treated at any time between harvest and sowing. It iscustomary to use seed which has been separated from the plant and freedfrom cobs, shells, stalks, coats, hairs or the flesh of the fruits. Forexample, it is possible to use seed which has been harvested, cleanedand dried down to a moisture content of less than 15% by weight.Alternatively, it is also possible to use seed which, after drying, forexample, has been treated with water and then dried again.

When treating the seed, it generally has to be ensured that the amountof the inventive composition applied to the seed and/or the amount offurther additives is selected such that the germination of the seed isnot impaired, or that the resulting plant is not damaged. This must beensured particularly in the case of active ingredients which can exhibitphytotoxic effects at certain application rates.

The inventive compositions can be applied directly, i.e. withoutcontaining any other components and without having been diluted. Ingeneral, it is preferable to apply the compositions to the seed in theform of a suitable formulation. Suitable formulations and methods forseed treatment are known to those skilled in the art and are described,for example, in the following documents: U.S. Pat. No. 4,272,417, U.S.Pat. No. 4,245,432, U.S. Pat. No. 4,808,430, U.S. Pat. No. 5,876,739, US2003/0176428, WO 2002/080675, WO 2002/028186.

The active ingredients usable in accordance with the invention can beconverted to the customary seed dressing formulations, such assolutions, emulsions, suspensions, powders, foams, slurries or othercoating compositions for seed, and also ULV formulations.

These formulations are prepared in a known manner, by mixing the activeingredients or active ingredient combinations with customary additives,for example customary extenders and solvents or diluents, dyes, wettingagents, dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins, and also water.

Useful dyes which may be present in the seed dressing formulationsusable in accordance with the invention are all dyes which are customaryfor such purposes. It is possible to use either pigments, which aresparingly soluble in water, or dyes, which are soluble in water.Examples include the dyes known by the names Rhodamine B, C.I. PigmentRed 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are conventionally used for theformulation of active agrochemical ingredients. Usable with preferenceare alkylnaphthalenesulphonates, such as diisopropyl- ordiisobutylnaphthalenesulphonates.

Useful dispersants and/or emulsifiers which may be present in the seeddressing formulations usable in accordance with the invention are allnonionic, anionic and cationic dispersants conventionally used for theformulation of active agrochemical ingredients. Usable with preferenceare nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Useful nonionic dispersants include especially ethyleneoxide/propylene oxide block polymers, alkylphenol polyglycol ethers andtristryrylphenol polyglycol ether, and the phosphated or sulphatedderivatives thereof. Suitable anionic dispersants are especiallylignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehydecondensates.

Antifoams which may be present in the seed dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for the formulation of active agrochemicalingredients. Silicone antifoams and magnesium stearate are usable withpreference.

Preservatives which may be present in the seed dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressingformulations usable in accordance with the invention are all substancesusable for such purposes in agrochemical compositions. Preferredexamples include cellulose derivatives, acrylic acid derivatives,xanthan, modified clays and finely divided silica.

Adhesives which may be present in the seed dressing formulations usablein accordance with the invention are all customary binders usable inseed dressing products. Preferred examples include polyvinylpyrrolidone,polyvinyl acetate, polyvinyl alcohol and tylose.

The gibberellins which may be present in the seed dressing formulationsusable in accordance with the invention may preferably be gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz- and Schadlingsbekampfungsmittel” [Chemistryof Crop Protection Agents and Pesticides], vol. 2, Springer Verlag,1970, p. 401-412).

The seed dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also the seed of maize, rice, oilseedrape, peas, beans, cotton, sunflowers, and beets, or else a wide varietyof different vegetable seed. The seed dressing formulations usable inaccordance with the invention, or the dilute preparations thereof, canalso be used to dress seed of transgenic plants. In this case,additional synergistic effects may also occur in interaction with thesubstances formed by expression.

For treatment of seed with the seed dressing formulations usable inaccordance with the invention, or the preparations prepared therefrom byadding water, all mixing units usable customarily for the seed dressingare useful. Specifically, the procedure in the seed dressing is to placethe seed into a mixer, to add the particular desired amount of seeddressing formulations, either as such or after prior dilution withwater, and to mix everything until the formulation is distributedhomogeneously on the seed. If appropriate, this is followed by a dryingoperation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the active ingredientsin the formulations and by the seed. The application rates of activeingredient combination are generally between 0.001 and 50 g per kilogramof seed, preferably between 0.01 and 15 g per kilogram of seed.

In addition, the inventive compounds of the formula (I) also have verygood antimycotic effects. They have a very broad antimycotic activityspectrum, especially against dermatophytes and yeasts, moulds anddiphasic fungi (for example against Candida species, such as Candidaalbicans, Candida glabrata), and Epidermophyton floccosum, Aspergillusspecies, such as Aspergillus niger and Aspergillus fumigatus,Trichophyton species, such as Trichophyton mentagrophytes, Microsporonspecies such as Microsporon canis and audouinii. The enumeration ofthese fungi by no means constitutes a restriction of the mycoticspectrum covered, and is merely of illustrative character.

The inventive active ingredients of the formula (I) can therefore beused both in medical and in non-medical applications.

The active ingredients can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is accomplished in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is also possible to apply the activeingredients by the ultra-low volume method, or to inject the activeingredient preparation or the active ingredient itself into the soil. Itis also possible to treat the seed of the plants.

When using the inventive active ingredients as fungicides, theapplication rates can be varied within a relatively wide range,depending on the kind of application. The application rate of theinventive active ingredients is

-   -   in the case of treatment of plant parts, for example leaves:        from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more        preferably from 50 to 300 g/ha (in the case of application by        watering or dripping, it is even possible to reduce the        application rate, especially when inert substrates such as        rockwool or perlite are used);    -   in the case of seed treatment: from 2 to 200 g per 100 kg of        seed, preferably from 3 to 150 g per 100 kg of seed, more        preferably from 2.5 to 25 g per 100 kg of seed, even more        preferably from 2.5 to 12.5 g per 100 kg of seed;    -   in the case of soil treatment: from 0.1 to 10 000 g/ha,        preferably from 1 to 5000 g/ha.

These application rates are merely by way of example and are notlimiting for the purposes of the invention.

The inventive active ingredients are used in the veterinary sector andin animal husbandry in a known manner, by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, for example by injection (intramuscular,subcutaneous, intravenous, intraperitoneal and the like), implants, bynasal administration, by dermal use in the form, for example, of dippingor bathing, spraying, pouring on and spotting on, washing and powdering,and also with the aid of moulded articles containing the activeingredient, such as collars, ear marks, tail marks, limb bands, halters,marking devices and the like.

When used for livestock, poultry, domestic animals and the like, theactive ingredients of the formula (I) can be used as formulations (forexample powders, emulsions, flowables) comprising the active ingredientsin an amount of 1 to 80% by weight, either directly or after 100 to 10000-fold dilution, or they may be used as a chemical bath.

The ready-to-use compositions may optionally also comprise otherinsecticides, and optionally also one or more fungicides.

With regard to possible additional mixing partners, reference is made tothe abovementioned insecticides and fungicides.

At the same time, the inventive compounds can be used for protection ofobjects which come into contact with saltwater or brackish water,especially hulls, screens, nets, buildings, moorings and signallingsystems, against fouling.

In addition, the inventive compounds can be used as anti-foulingcompositions, alone or in combinations with other active ingredients.

The inventive treatment method can be used in the treatment ofgenetically modified organisms (GMOs), e.g. plants or seeds. Geneticallymodified plants (or transgenic plants) are plants of which aheterologous gene has been stably integrated into the genome. Theexpression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using, for example,antisense technology, cosuppression technology or RNAinterference—RNAi—technology). A heterologous gene that is located inthe genome is also called a transgene. A transgene that is defined byits particular location in the plant genome is called a transformationor transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the active ingredients and compositions which can be usedaccording to the invention, better plant growth, increased tolerance tohigh or low temperatures, increased tolerance to drought or to water orsoil salt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, largerplant height, greener leaf colour, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products are possible, which exceed theeffects which were actually to be expected.

At certain application rates, the active ingredient combinationsaccording to the invention may also have a strengthening effect inplants. Accordingly, they are suitable for mobilizing the defence systemof the plant against attack by unwanted phytopathogenic fungi and/ormicroorganisms and/or viruses. This may, if appropriate, be one of thereasons of the enhanced activity of the combinations according to theinvention, for example against fungi. Plant-strengthening(resistance-inducing) substances are to be understood as meaning, in thepresent context, those substances or combinations of substances whichare capable of stimulating the defence system of plants in such a waythat, when subsequently inoculated with unwanted phytopathogenic fungiand/or microorganisms and/or viruses, the treated plants display asubstantial degree of resistance to these unwanted phytopathogenic fungiand/or microorganisms and/or viruses. In the present case, unwantedphytopathogenic fungi and/or microorganisms and/or viruses areunderstood to mean phytopathogenic fungi, bacteria and viruses. Thus,the substances according to the invention can be employed for protectingplants against attack by the abovementioned pathogens within a certainperiod of time after the treatment. The period of time within whichprotection is effected generally extends from 1 to 10 days, preferably 1to 7 days, after the treatment of the plants with the activeingredients.

Plants and plant cultivars which are preferably treated according to theinvention include all plants which have genetic material which impartsparticularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably treated accordingto the invention are resistant against one or more biotic stresses, i.e.said plants show a better defence against animal and microbial pests,such as against nematodes, insects, mites, phytopathogenic fungi,bacteria, viruses and/or viroids.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozone exposure,high light exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including, but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigour, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristics of heterosis or hybrid vigourwhich results in generally higher yield, vigour, health and resistancetowards biotic and abiotic stresses. Such plants are typically made bycrossing an inbred male-sterile parent line (the female parent) withanother inbred male-fertile parent line (the male parent). Hybrid seedis typically harvested from the male-sterile plants and sold to growers.Male-sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or male flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants which contain the genetic determinants responsible for malesterility is fully restored. This can be accomplished by ensuring thatthe male parents have appropriate fertility restorer genes which arecapable of restoring the male fertility in hybrid plants that containthe genetic determinants responsible for male sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species. However, genetic determinants for male sterilitycan also be located in the nuclear genome. Male-sterile plants can alsobe obtained by plant biotechnology methods such as genetic engineering.A particularly useful means of obtaining male-sterile plants isdescribed in WO 89/10396 in which, for example, a ribonuclease such asbarnase is selectively expressed in the tapetum cells in the stamens.Fertility can then be restored by expression in the tapetum cells of aribonuclease inhibitor such as barstar.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.For example, glyphosate-tolerant plants can be obtained by transformingthe plant with a gene encoding the enzyme5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of suchEPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonellatyphimurium, the CP4 gene of the bacterium Agrobacterium sp., the genesencoding a petunia EPSPS, a tomato EPSPS, or an eleusine EPSPS. It canalso be a mutated EPSPS. Glyphosate-tolerant plants can also be obtainedby expressing a gene that encodes a glyphosate oxidoreductase enzyme.Glyphosate-tolerant plants can also be obtained by expressing a genethat encodes a glyphosate acetyltransferase enzyme. Glyphosate-tolerantplants can also be obtained by selecting plants containingnaturally-occurring mutations of the above-mentioned genes.

Other herbicide-resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedby expressing an enzyme detoxifying the herbicide or a mutant glutaminesynthase enzyme that is resistant to inhibition. One such efficientdetoxifying enzyme is an enzyme encoding a phosphinothricinacetyltransferase (such as the bar or pat protein from Streptomycesspecies). Plants expressing an exogenous phosphinothricinacetyltransferase have been described.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase(HPPD). Hydroxyphenylpyruvatedioxygenases are enzymes that catalyse thereaction in which para-hydroxyphenylpyruvate (HPP) is transformed intohomogentisate. Plants tolerant to HPPD inhibitors can be transformedwith a gene encoding a naturally-occurring resistant HPPD enzyme, or agene encoding a mutated HPPD enzyme. Tolerance to HPPD inhibitors canalso be obtained by transforming plants with genes encoding certainenzymes enabling the formation of homogentisate despite the inhibitionof the native HPPD enzyme by the HPPD inhibitor. Tolerance of plants toHPPD inhibitors can also be improved by transforming plants with a geneencoding an enzyme prephenate dehydrogenase in addition to a geneencoding an HPPD-tolerant enzyme.

Further herbicide-resistant plants are plants that are made tolerant toacetolactate synthase (ALS) inhibitors. Known ALS inhibitors include,for example, sulphonylurea, imidazolinone, triazolopyrimidines,pyrimidinyloxy(thio)benzoates, and/or sulphonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides. The production ofsulphonylurea-tolerant plants and imidazolinone-tolerant plants isdescribed in international publication WO 1996/033270. Furthersulphonylurea- and imidazolinone-tolerant plants are also described, forexample, in WO 2007/024782.

Other plants tolerant to imidazolinone and/or sulphonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, includes anyplant containing at least one transgene comprising a coding sequenceencoding:

-   1) an insecticidal crystal protein from Bacillus thuringiensis or an    insecticidal portion thereof, such as the insecticidal crystal    proteins described online at:    http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/, or    insecticidal portions thereof, e.g., proteins of the Cry protein    classes Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or    insecticidal portions thereof; or-   2) a crystal protein from Bacillus thuringiensis or a portion    thereof which is insecticidal in the presence of a second other    crystal protein from Bacillus thuringiensis or a portion thereof,    such as the binary toxin made up of the Cy34 and Cy35 crystal    proteins; or-   3) a hybrid insecticidal protein comprising parts of two different    insecticidal crystal proteins from Bacillus thuringiensis, such as a    hybrid of the proteins of 1) above or a hybrid of the proteins of 2)    above, e.g., the Cry1A.105 protein produced by corn event MON98034    (WO 2007/027777); or-   4) a protein of any one of 1) to 3) above wherein some, particularly    1 to 10, amino acids have been replaced by another amino acid to    obtain a higher insecticidal activity to a target insect species,    and/or to expand the range of target insect species affected, and/or    because of changes introduced into the encoding DNA during cloning    or transformation, such as the Cry3Bb1 protein in corn events MON863    or MON88017, or the Cry3A protein in corn event MIR 604;-   5) an insecticidal secreted protein from Bacillus thuringiensis or    Bacillus cereus, or an insecticidal portion thereof, such as the    vegetative insecticidal proteins (VIP) listed at:    http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html,    e.g., proteins from the VIP3Aa protein class; or-   6) a secreted protein from Bacillus thuringiensis or Bacillus cereus    which is insecticidal in the presence of a second secreted protein    from Bacillus thuringiensis or B. cereus, such as the binary toxin    made up of the VIP1A and VIP2A proteins.-   7) a hybrid insecticidal protein comprising parts from different    secreted proteins from Bacillus thuringiensis or Bacillus cereus,    such as a hybrid of the proteins in 1) above or a hybrid of the    proteins in 2) above; or-   8) a protein of any one of 1) to 3) above wherein some, particularly    1 to 10, amino acids have been replaced by another amino acid to    obtain a higher insecticidal activity to a target insect species,    and/or to expand the range of target insect species affected, and/or    because of changes introduced into the encoding DNA during cloning    or transformation (while still encoding an insecticidal protein),    such as the VIP3Aa protein in cotton event COT 102.

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 8. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 8, to expand the range oftarget insect species affected or to delay insect resistance developmentto the plants by using different proteins insecticidal to the sametarget insect species but having a different mode of action, such asbinding to different receptor binding sites in the insect.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants include:

-   a. plants which contain a transgene capable of reducing the    expression and/or the activity of the poly(ADP-ribose) polymerase    (PARP) gene in the plant cells or plants;-   b. plants which contain a stress tolerance enhancing transgene    capable of reducing the expression and/or the activity of the PARG    encoding genes of the plants or plant cells;-   c. plants which contain a stress tolerance enhancing transgene    coding for a plant-functional enzyme of the nicotinamide adenine    dinucleotide salvage biosynthesis pathway    -   including nicotinamidase, nicotinate phosphoribosyltransferase,        nicotinic acid mononucleotide adenyltransferase, nicotinamide        adenine dinucleotide synthetase or nicotinamide        phosphoribosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   1) transgenic plants which synthesize a modified starch, which in    its physical-chemical characteristics, in particular the amylose    content or the amylose/amylopectin ratio, the degree of branching,    the average chain length, the side chain distribution, the viscosity    behaviour, the gelling strength, the starch grain size and/or the    starch grain morphology, is changed in comparison with the    synthesized starch in wild type plant cells or plants, so that this    modified starch is better suited for special applications.-   2) transgenic plants which synthesize non-starch carbohydrate    polymers or which synthesize non-starch carbohydrate polymers with    altered properties in comparison to wild type plants without genetic    modification. Examples are plants producing polyfructose, especially    of the inulin and levan type, plants producing alpha-1,4-glucans,    plants producing alpha-1,6 branched alpha-1,4-glucans, plants    producing alternan.-   3) transgenic plants which produce hyaluronan.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as cotton plants, with altered fibrecharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants containing a mutation imparting such alteredfibre characteristics and include:

-   a) plants, such as cotton plants, containing an altered form of    cellulose synthase genes;-   b) plants, such as cotton plants, containing an altered form of rsw2    or rsw3 homologous nucleic acids;-   c) plants, such as cotton plants, with increased expression of    sucrose phosphate synthase;-   d) plants, such as cotton plants, with increased expression of    sucrose synthase;-   e) plants, such as cotton plants, wherein the timing of the    plasmodesmatal gating at the basis of the fibre cell is altered,    e.g. through downregulation of fibre-selective β-1,3-glucanase;-   f) plants, such as cotton plants, having fibres with altered    reactivity, e.g. through the expression of    N-acetylglucosaminetransferase gene including nodC and chitin    synthase genes.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are plants, such as oilseed rape or related Brassica plants,with altered oil profile characteristics. Such plants can be obtained bygenetic transformation, or by selection of plants containing a mutationimparting such altered oil characteristics and include:

-   a) plants, such as oilseed rape plants, producing oil having a high    oleic acid content;-   b) plants, such as oilseed rape plants, which produce oil having a    low linolenic acid content;-   c) plants, such as oilseed rape plants, producing oil having a low    level of saturated fatty acids.

Particularly useful transgenic plants which may be treated according tothe invention are plants which comprise one or more genes which encodeone or more toxins, and are the transgenic plants which are sold underthe following trade names: YIELD GARD® (for example maize, cotton, soybeans), KnockOut® (for example maize), BiteGard® (for example maize),BT-Xtra® (for example maize), StarLink® (for example maize), Bollgard®(cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (forexample maize), Protecta® and NewLeaf® (potatoes). Examples ofherbicide-tolerant plants which should be mentioned are corn varieties,cotton varieties and soybean varieties which are available under thefollowing trade names: Roundup Ready® (glyphosate tolerance, for examplemaize, cotton, soya bean), Liberty Link® (phosphinotricin tolerance, forexample oilseed rape), IMI® (imidazolinone tolerance) and SCS®(sulphonylurea tolerance), for example maize. Herbicide-resistant plants(plants bred in a conventional manner for herbicide tolerance) whichshould be mentioned include the varieties sold under the Clearfield®name (for example maize).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, or acombination of transformation events, and that are listed for example inthe databases for various national or regional regulatory agencies (seefor example http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

The plants listed can be treated in accordance with the invention in aparticularly advantageous manner with the compounds of the generalformula (I) and/or the active ingredient mixtures according to theinvention. The preferred ranges stated above for the active ingredientsor mixtures also apply to the treatment of these plants. Particularemphasis is given to the treatment of plants with the compounds ormixtures specifically mentioned in the present text.

The inventive active ingredients or compositions can thus be used toprotect plants from attack by the pathogens mentioned for a certainperiod of time after treatment. The period for which protection isprovided extends generally for 1 to 28 days, preferably for 1 to 14days, particularly preferably for 1 to 10 days, very particularlypreferably for 1 to 7 days after the treatment of the plants with theactive ingredients, or for up to 200 days after a seed treatment.

The preparation and the use of the inventive active ingredients of theformula (I) is illustrated by the examples which follow. However, theinvention is not limited to these examples.

General notes: Unless stated otherwise, all chromatographic purificationand separation steps are carried out on silica gel and using a solventgradient from 0:100 ethyl acetate/cyclohexane to 100:0 ethylacetate/cyclohexane.

Preparation of Compound (I-5) Step 1 tert-Butyl4-[4-(5-{2-[(methylsulphonyl)amino]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate(XVIIf-1)

To a solution of tert-butyl4-{4-[(Z/E)-(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate(1.35 g) and N-(2-vinylphenyl)methanesulphonamide (1.11 g) in ethylacetate (20 ml) were added, at room temperature, potassiumhydrogencarbonate (2.17 g) and N-chlorosuccinimide (0.58 g) and thenthree drops of water. The reaction mixture was stirred at 50° C.overnight, then ethyl acetate and water were added, and the mixture wasextracted with ethyl acetate. The organic extracts were dried oversodium sulphate and concentrated under reduced pressure. The residue waspurified by chromatography. This gave tert-butyl4-[4-(5-{2-[(methylsulphonyl)amino]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate(0.94 g).

Step 24-[4-(5-{2-[(Methylsulphonyl)ammonio]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidiniumdichloride (XIIIb-1)

To a solution of tert-butyl4-[4-(5-{2-[(methylsulphonyl)amino]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate(900 mg) in 1,4-dioxane (10 ml) was added dropwise, at 0° C., a 4 molarsolution of hydrogen chloride in 1,4-dioxane (6.66 ml). The reactionmixture was stirred at 0° C. and then gradually warmed to roomtemperature. After stirring overnight, the solvent and excess hydrogenchloride were removed. This gave4-[4-(5-{2-[(methylsulphonyl)ammonio]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidiniumdichloride (1.00 g).

Step 3N-(2-{3-[2-(1-{[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl)methanesulphonamide(I-5)

4-[4-(5-{2-[(Methylsulphonyl)ammonio]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidiniumdichloride (201 mg),[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetic acid (104 mg) andtriethylamine (51 mg) are dissolved in dichloromethane (10 ml) and themixture is stirred for 10 min. The mixture is stirred for a further 10min, before bromotris(pyrrolidino)phosphonium hexafluorophosphate (254mg) is added. The reaction mixture is stirred at room temperature for 2hours. After removal of the solvent under reduced pressure, the residueis purified by chromatography. This givesN-(2-{3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl)methanesulphonamide(107 mg).

Preparation of Compound (I-4) Step 1N-(2-{3-[2-(1-{[2,5-Bis(difluoromethyl)phenyl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl)methanesulphonamide(I-4)

4-[4-(5-{2-[(Methylsulphonyl)ammonio]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidiniumdichloride (298 mg) and [2,5-bis(difluoromethyl)phenyl]acetic acid (175mg) were converted analogously to I-5 (step 3). This gaveN-(2-{3-[2-(1-{[2,5-bis(difluoromethyl)phenyl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl)methanesulphonamide(170 mg).

Preparation of Compound (I-6) Step 1N-[2,5-Bis(difluoromethyl)phenyl]-4-[4-(5-{2-[(methylsulphonyl)amino]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboxamide(I-6)

To a suspension of4-[4-(5-{2-[(methylsulphonyl)ammonio]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidiniumdichloride (202 mg) in dichloromethane (5 ml) and triethylamine (51 mg)at room temperature were added1,4-bis(difluoromethyl)-2-isocyanatobenzene (100 mg) and one drop of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The mixture was stirred atroom temperature for 2 hours, and then saturated ammonium chloridesolution was added. The aqueous phase was removed and extracted withethyl acetate. The combined organic phases were dried over sodiumsulphate and concentrated under reduced pressure. The residue waspurified by chromatography. This gaveN-[2,5-bis(difluoromethyl)phenyl]-4-[4-(5-{2-[(methylsulphonyl)amino]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidine-1-carboxamide(150 mg).

Preparation of Compounds of the Formula (I-3) Step 1 tert-Butyl4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate(XVIIf-2)

To a solution of tert-butyl4-{4-[(Z/E)-(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate(5.6 g) and 2-vinylbenzaldehyde (2.61 g) in ethyl acetate (70 ml) atroom temperature were added potassium hydrogencarbonate (7.23 g) andN-chlorosuccinimide (2.31 g), and then three drops of water. Thereaction mixture was stirred at 60° C. for 3 hours, then ethyl acetateand water were added, and the mixture was extracted with ethyl acetate.The organic extracts were dried over sodium sulphate and concentratedunder reduced pressure. The residue was purified by chromatography. Thedeveloped product is tert-Butyl4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate(5.69 g).

Step 24-{4-[5-(2-Formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidiniumchloride (XIIIb-2)

tert-Butyl4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate(5.1 g) was converted analogously to 1-5 (step 2). This gave4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidiniumchloride (4.35 g).

Step 3N-(5-Chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide(I-3)

To a suspension of4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidiniumchloride (1.44 g) in dichloromethane (30 ml) and diisopropylethylamine(0.73 ml) at room temperature were added4-chloro-2-isocyanato-1-methylbenzene (700 mg) and one drop of1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The mixture was stirred atroom temperature overnight, and water was then added. The aqueous phasewas removed and extracted with ethyl acetate. The combined organicphases were dried over sodium sulphate and concentrated under reducedpressure. The residue was purified by chromatography. This gaveN-(5-chloro-2-methylphenyl)-4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxamide(1.23 g).

Preparation of Compound (I-7)2-{3-[2-(1-{[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde(I-7)

To a solution of [5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]aceticacid (900 mg) in dichloromethane (20 ml) are added, at 0° C., oxalylchloride (1.50 g) and one drop of N,N-dimethylformamide. The reactionmixture is stirred at room temperature for 2 hours. The solvent and theexcess reagent are removed under reduced pressure. The solid residue isdissolved again in dichloromethane and added dropwise at 0° C. to asolution of4-{4-[5-(2-formylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidiniumchloride (1.49 g) and diisopropylethylamine (2.05 ml) in dichloromethane(20 ml). The reaction mixture is stirred at room temperature overnight.Then concentrated sodium hydrogencarbonate solution is added thereto,and the aqueous phase is removed and extracted with ethyl acetate. Thecombined organic phases are dried over sodium sulphate and concentrated.Purification by column chromatography gives2-{3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde(2.00 g).

EXAMPLES

The structural elements G¹ and Q²⁴-3 listed in Table 1 are defined asfollows:

For all compounds listed in Table 1, p=0 and L²=direct bond, R²═H

TABLE 1 Ex. A L1 Y X G R_(G1) Q R⁵ R¹ Log P 1 5-methyl-3- CH₂ O C G¹ HQ²⁴-3 H 3-formylphenyl 2.83[a] (trifluoromethyl)-1H- pyrazol-1-yl 25-chloro-2-methylphenyl NH O C G¹ H Q²⁴-3 H 3-formylphenyl 3.05[a] 35-chloro-2-methylphenyl NH O C G¹ H Q²⁴-3 H 2-formylphenyl 3.35[a] 42,5- CH₂ O C G¹ H Q²⁴-3 H 2- 2.81[a] bis(difluoromethyl)phenyl[(methylsulphonyl) amino]phenyl 5 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-(trifluoromethyl)-1H- [(methylsulphonyl) pyrazol-1-yl amino]phenyl 62,5- NH O C G¹ H Q²⁴-3 H 2- 2.72[a] bis(difluoromethyl)phenyl[(methylsulphonyl) amino]phenyl 7 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H2-formylphenyl 3.12[a] trifluoromethyl)-1H- pyrazol-1-yl 8 5-methyl-3-CH₂ O C G¹ H Q²⁴-3 H 2,6-difluoro-3-(prop-2- (trifluoromethyl)-1H-yn-1-yloxy)phenyl pyrazol-1-yl 9 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H3-fluoro-2-(prop-2-yn- (trifluoromethyl)-1H- 1-ylox)phenyl pyrazol-1-yl10 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 3-(prop-2-yn-1- 3.49[a];(trifluoromethyl)-1H- yloxy)phenyl 3.3[b] pyrazol-1-yl 11 5-methyl-3-CH₂ O C G¹ H Q²⁴-3 H 2-chloro-6-(prop-2-yn- 3.62[a];(trifluoromethyl)-1H- 1-yloxy)phenyl 3.53[b] pyrazol-1-yl 12 5-methyl-3-CH₂ O C G¹ H Q²⁴-3 H 2-fluoro-6-(prop-2-yn- 3.35[a];(trifluoromethyl)-1H- 1-yloxy)phenyl 3.27[b] pyrazol-1-yl 13 5-methyl-3-CH₂ O C G¹ H Q²⁴-3 H 2-(prop-2-yn-1- 3.47[a]; (trifluoromethyl)-1H-yloxy)phenyl 3.37[b] pyrazol-1-yl 14 3,5-bis(trifluoromethyl)- CH₂ O CG¹ H Q²⁴-3 H 2-[(cyclopropylcarbonyl) 4.04[a] 1H-pyrazol-1-yl oxy]phenyl15 3-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H 2-(but-2-yn-1-yloxy)-3.28[a] methyl-1H-pyrazol-1-yl 4-methoxyphenyl 163,5-bis(trifluoromethyl)- CH₂ O C G¹ H Q²⁴-3 H 2-(cyclopropylmethoxy)4.59[a] 1H-pyrazol-1-yl phenyl 17 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-4.03[a] (trifluoromethyl)-1H- (cyclopropylmethoxy) pyrazol-1-yl phenyl18 5-(difluoromethyl)-3- CH₂ O C G¹ H Q²⁴-3 H 2-(allyloxy)phenyl3.42[a]; methyl-1H-pyrazol-1-yl 3.33[b] 19 5-methyl-3- CH₂ O C G¹ HQ²⁴-3 H 3-(allyloxy)-2,6- (trifluoromethyl)-1H- difluorophenylpyrazol-1-yl 20 3-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H4-chloro-2-(prop-2-yn- 3.37[a]; methyl-1H-pyrazol-1-yl 1-yloxy)phenyl3.36[b] 21 3-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H2,4-dichloro-6-(prop-2- 3.66[a]; methyl-1H-pyrazol-1-ylyn-1-yloxy)phenyl 3.57[b] 22 3-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H2-(allyloxy)-4- 3.62[a]; methyl-1H-pyrazol-1-yl methylphenyl 3.66[b]; 233-(difluoromethyl-5- CH₂ O C G¹ H Q²⁴-3 H 4-methyl-2-(prop-2-yn-3.23[a]; methyl-1H-pyrazol-1-yl 1-yloxy)phenyl 3.23[b]; 243-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H 2-(allyloxy)-4,6- 3.95[a];methyl-1H-pyrazol-1-yl dichlorophenyl 3.97[b]; 25 2,5-dimethylphenyl NHO C G¹ H Q²⁴-3 H 2-(allyloxy)-6- 3.64[a]; fluorophenyl 3.62[b] 265-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 4-methyl-2-(prop-2-yn- 3.67[a];(trifluoromethyl)-1H- 1-yloxy)phenyl 3.61[b] pyrazol-1-yl 273-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H 2- 3.5[a]methyl-1H-pyrazol-1-yl (cyclopropylmethoxy)- 4-methoxyphenyl 283-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H 2- 3.44[a]methyl-1H-pyrazol-1-yl (cyclopropylmethoxy)- 6-fluorophenyl 295-(difluoromethyl)-3- CH₂ O C G¹ H Q²⁴-3 H 2-(prop-2-yn-1- 3.03[a]methyl-1H-pyrazol-1-yl yloxy)phenyl 30 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H2-(allyloxy)phenyl 3.86[a]; (trifluoromethyl)-1H- 3.73[b] pyrazol-1-yl31 3-(difluoromethyl)-5- CH₂ O C G¹ H Q²⁴-3 H 2-fluoro-6-(prop-2-yn-2.92[a] methyl-1H-pyrazol-1-yl 1-yloxy)phenyl 323,5-bis(trifluoromethyl)- CH₂ O C G¹ H Q²⁴-3 H 2-(prop-2-yn-1- 3.91[a]1H-pyrazol-1-yl yloxy)phenyl 33 3,5-bis(trifluoromethyl)- CH₂ O C G¹ HQ²⁴-3 H 2-(allyloxy)phenyl 4.38[a] 1H-pyrazol-1-yl 34 5-methyl-3- CH₂ OC G¹ H Q²⁴-3 H 2- 2.6[a] (trifluoromethyl)-1H- [methylsulphonyl)pyrazol-1-yl methyl]phenyl 35 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-2.34[a] (trifluoromethyl)-1H- [(methylsulphinyl) pyrazol-1-ylmethyl]phenyl 36 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2- 2.53[a](trifluoromethyl)-1H- [(ethylsulphinyl)methyl] pyrazol-1-yl phenyl 375-(difluoromethyl)-3- CH₂ O C G¹ H Q²⁴-3 CH₃ 2-fluoro-6-(prop-2-yn-3.11[a]; methyl-1H-pyrazol-1-yl 1-yloxy)phenyl 3.12[b]; 382,5-dimethylphenyl NH O C G¹ H Q²⁴-3 H 2-chloro-6-(prop-2-yn- 3.68[a];1-yloxy)phenyl 3.57[b] 39 5-chloro-2-methylphenyl NH O C G¹ H Q²⁴-3 H2-(allyloxy)-6- 4.21[a]; chlorophenyl 4.11[b] 40 5-methyl-3- CH₂ O C G¹H Q²⁴-3 H 3-[(cyclopropylcarbonyl) 3.53[a]; (trifluoromethyl)-1H-oxy]phenyl 3.47[b] pyrazol-1-yl 41 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H3-(allyloxy)phenyl 3.62[a]; (trifluoromethyl)-1H- 3.68[b]; pyrazol-1-yl42 2,5-dimethylphenyl NH O C G¹ H Q²⁴-3 H 2-(allyloxy)-6- 3.98[a];chlorophenyl 3.91[b] 43 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-[2,2,2-3.77[a] (trifluoromethyl)-1H- trifluoroethoxy)methyl] pyrazol-1-ylphenyl 44 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-[(2- 3.28[a](trifluoromethyl)-1H- methoxyethoxy)methyl] pyrazol-1-yl phenyl 452,5-dimethylphenyl NH O C G¹ H Q²⁴-3 H 2-(prop-2-yn-1- 3.43[a];yloxy)phenyl 3.41[b] 46 2,5-dimethylphenyl NH O C G¹ H Q²⁴-3 H2-(allyloxy)phenyl 3.91[a]; 3.81[b] 47 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H4- 3.49[a]; (trifluoromethyl)-1H- [(cyclopropylcarbonyl) 3.4[b]pyrazol-1-yl oxy]phenyl 48 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-chloro-6-3.73[a]; (trifluoromethyl)-1H- [(cyclopropylcarbonyl) 3.64[b]pyrazol-1-yl oxy]phenyl 49 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H2-fluoro-6-(2- 3.28[a]; (trifluoromethyl)-1H- methoxyethoxy)phenyl3.17[b] pyrazol-1-yl 50 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-(allyloxy)-6-3.94[a]; (trifluoromethyl)-1H- chlorophenyl 3.83[b] pyrazol-1-yl 515-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-(allyloxy)-6- 3.7[a];(trifluoromethyl)-1H- fluorophenyl 3.61[b] pyrazol-1-yl 52 5-methyl-3-CH₂ O C G¹ H Q²⁴-3 H 2-(allyloxy)-3- 3.97[a]; (trifluoromethyl)-1H-fluorophenyl 3.84[b] pyrazol-1-yl 53 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H2-fluoro-6- 3.03[a]; (trifluoromethyl)-1H- formylphenyl 2.95[b]pyrazol-1-yl 54 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2- 3.62[a];(trifluoromethyl)-1H- [(cyclopropylcarbonyl) 3.5[b] pyrazol-1-yloxy]-3-fluorophenyl 55 5-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2-(2- 3.27[a];(trifluoromethyl)-1H- methoxyethoxy)phenyl 3.25[b] pyrazol-1-yl 565-methyl-3- CH₂ O C G¹ H Q²⁴-3 H 2- 3.52[a]; (trifluoromethyl)-1H-[(cyclopropylcarbonyl) 3.41[b] pyrazol-1-yl oxy]phenyl

The logP values were measured according to EEC directive 79/831 AnnexV.A8 by HPLC (High Performance Liquid Chromatography) on reversed-phasecolumns (C 18), using the methods below:

-   ^([a]) The LC-MS determination in the acidic range is effected at pH    2.7 with 0.1% aqueous formic acid and acetonitrile (contains 0.1%    formic acid) as eluents; linear gradient from 10% acetonitrile to    95% acetonitrile.-   ^([b]) The LC-MS determination in the neutral range is effected at    pH 7.8 using 0.001 molar aqueous ammonium hydrogencarbonate solution    and acetonitrile as eluents; linear gradient from 10% acetonitrile    to 95% acetonitrile.

The calibration is effected with unbranched alkan-2-ones (having 3 to 16carbon atoms) with known logP values (logP values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The lambda-max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm

NMR Data of Selected Examples NMR Peak List Method

The 1H NMR data of selected examples are stated in the form of 1H NMRpeak lists. For each signal peak, first the 8 value in ppm and then thesignal intensity in round brackets are listed. The 8 value—signalintensity number pairs for different signal peaks are listed withseparation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

Ex. 1, Solvent: DMSO, Spectrometer: 399.95 MHz

10.0344 (6.63); 8.0579 (0.79); 8.0400 (6.68); 7.9295 (3.74); 7.8988(2.27); 7.8831 (2.00); 7.8801 (2.32); 7.7478 (1.88); 7.7285 (2.24);7.6635 (2.24); 7.6446 (2.92); 7.6255 (1.19); 6.4922 (4.46); 5.8980(1.40); 5.8784 (1.71); 5.8708 (1.52); 5.8515 (1.21); 5.3605 (0.36);5.3405 (0.97); 5.2983 (2.90); 5.2496 (2.81); 5.2072 (0.87); 4.3847(1.15); 4.3527 (1.13); 4.0571 (0.96); 4.0393 (2.31); 4.0216 (2.35);4.0036 (1.55); 3.9837 (2.26); 3.9560 (2.66); 3.9405 (1.98); 3.9130(1.45); 3.4474 (1.79); 3.4278 (2.00); 3.4041 (2.39); 3.3845 (3.03);3.3262 (49.36); 3.3125 (313.38); 3.2424 (1.57); 2.8718 (0.91); 2.8449(1.44); 2.8143 (0.81); 2.6743 (0.45); 2.6701 (0.49); 2.5053 (62.03);2.5010 (65.38); 2.3326 (0.53); 2.3277 (0.56); 2.2097 (16.00); 2.1319(1.48); 2.1068 (2.42); 2.0766 (1.41); 2.0049 (1.06); 2.0012 (1.21);1.9971 (1.55); 1.9870 (8.57); 1.8437 (0.61); 1.8238 (1.08); 1.7936(0.95); 1.7640 (0.44); 1.6093 (0.63); 1.5889 (1.03); 1.5799 (1.02);1.5581 (0.98); 1.5287 (0.44); 1.1930 (2.83); 1.1854 (0.97); 1.1752(4.77); 1.1574 (2.31); −0.0002 (1.06);

Ex. 2, Solvent: DMSO, Spectrometer: 399.95 MHz

10.0350 (7.37); 9.9023 (0.41); 8.6412 (0.39); 8.1288 (3.28); 8.0347(7.77); 7.9318 (3.17); 7.9024 (1.25); 7.8992 (1.80); 7.8956 (1.04);7.8836 (1.44); 7.8803 (2.04); 7.8768 (1.27); 7.7490 (1.35); 7.7328(1.52); 7.7297 (1.99); 7.6636 (1.95); 7.6446 (2.84); 7.6256 (1.17);7.3336 (3.23); 7.3281 (3.30); 7.1991 (2.18); 7.1786 (2.94); 7.0833(2.27); 7.0777 (2.14); 7.0630 (1.58); 7.0574 (1.50); 5.8976 (1.13);5.8781 (1.35); 5.8703 (1.29); 5.8507 (1.16); 4.1731 (1.81); 4.1396(1.90); 4.0578 (1.32); 4.0400 (3.70); 4.0222 (3.72); 4.0044 (1.30);3.9854 (1.31); 3.9578 (1.48); 3.9421 (1.68); 3.9147 (1.44); 3.4505(1.74); 3.4309 (1.76); 3.4073 (1.67); 3.3878 (1.85); 3.3567 (1.71);3.3193 (212.77); 3.0448 (1.07); 3.0392 (1.19); 3.0104 (2.19); 2.9815(1.25); 2.5411 (0.60); 2.5108 (12.77); 2.5065 (22.65); 2.5021 (28.64);2.4977 (19.62); 2.4934 (9.27); 2.1877 (0.40); 2.1557 (15.50); 2.0936(1.51); 2.0679 (1.65); 1.9877 (16.00); 1.7197 (0.52); 1.7101 (0.66);1.6880 (1.28); 1.6799 (1.42); 1.6579 (1.27); 1.6495 (1.19); 1.6282(0.48); 1.6190 (0.39); 1.1935 (4.47); 1.1757 (8.72); 1.1579 (4.30);−0.0002 (0.43);

Ex. 3, Solvent: DMSO, Spectrometer: 399.95 MHz

10.1834 (6.76); 8.1195 (3.33); 8.0328 (1.90); 8.0289 (1.95); 8.0231(0.70); 8.0126 (2.50); 8.0099 (2.53); 8.0020 (8.12); 7.7367 (0.79);7.7335 (0.83); 7.7178 (2.01); 7.6990 (1.52); 7.6957 (1.42); 7.6241(1.99); 7.6159 (2.62); 7.6074 (2.57); 7.5974 (1.90); 7.5894 (1.20);7.3298 (3.23); 7.3243 (3.27); 7.1963 (2.20); 7.1758 (2.98); 7.0813(2.24); 7.0758 (2.11); 7.0610 (1.60); 7.0554 (1.51); 6.4452 (1.19);6.4290 (1.35); 6.4174 (1.33); 6.4011 (1.21); 4.1613 (1.78); 4.1278(1.89); 4.0899 (1.41); 4.0620 (1.65); 4.0462 (1.79); 4.0401 (1.35);4.0222 (1.56); 4.0185 (1.60); 4.0045 (0.46); 3.3155 (190.78); 3.2923(3.19); 3.2755 (1.02); 3.2660 (0.58); 3.2268 (1.72); 3.2106 (1.68);3.1831 (1.57); 3.1669 (1.55); 3.0251 (1.23); 2.9958 (2.25); 2.9668(1.27); 2.5107 (11.92); 2.5065 (21.69); 2.5020 (27.90); 2.4977 (19.76);2.4935 (9.77); 2.1503 (16.00); 2.0743 (1.51); 2.0485 (1.71); 1.9879(4.94); 1.6994 (0.51); 1.6904 (0.61); 1.6686 (1.31); 1.6612 (1.39);1.6386 (1.30); 1.6311 (1.21); 1.6090 (0.50); 1.5996 (0.40); 1.1935(1.36); 1.1758 (2.65); 1.1580 (1.31); −0.0002 (2.28);

Ex. 4, Solvent: DMSO, Spectrometer: 399.95 MHz

9.2859 (0.81); 8.0295 (0.39); 8.0173 (6.58); 7.7187 (1.27); 7.6986(1.91); 7.6011 (1.48); 7.5812 (1.08); 7.5052 (2.29); 7.4373 (1.17);7.4208 (1.52); 7.4168 (1.40); 7.4057 (0.47); 7.3939 (0.45); 7.3784(1.58); 7.3680 (2.66); 7.3618 (4.78); 7.3593 (4.89); 7.3491 (1.42);7.3429 (1.39); 7.3367 (1.18); 7.3266 (0.51); 7.3204 (0.50); 7.2856(1.04); 7.2187 (1.17); 7.1489 (2.16); 7.0796 (2.37); 7.0128 (1.09);6.9403 (1.18); 6.1207 (0.97); 6.0995 (1.21); 6.0927 (1.20); 6.0723(1.00); 5.7464 (4.98); 4.4407 (0.61); 4.4116 (0.63); 4.0778 (0.63);4.0485 (0.87); 4.0392 (0.98); 4.0115 (2.08); 3.9904 (1.99); 3.9505(1.30); 3.9228 (1.16); 3.9068 (1.34); 3.8789 (1.04); 3.3752 (1.57);3.3642 (2.39); 3.3080 (1524.29); 3.2856 (11.89); 3.2635 (3.70); 3.2426(2.20); 3.2286 (1.24); 3.2084 (0.77); 3.1559 (0.42); 3.1400 (0.52);3.0603 (1.03); 3.0358 (16.00); 2.9393 (0.46); 2.8903 (1.36); 2.8331(0.56); 2.7997 (0.92); 2.7683 (0.57); 2.7316 (1.19); 2.6739 (1.32);2.6692 (1.64); 2.6647 (1.30); 2.5392 (2.28); 2.5221 (7.36); 2.5090(93.05); 2.5046 (173.22); 2.5002 (226.03); 2.4958 (157.39); 2.4914(75.79); 2.3316 (1.14); 2.3269 (1.48); 2.3224 (1.12); 2.0849 (1.22);2.0691 (1.99); 1.9867 (1.36); 1.9079 (0.38); 1.7282 (0.53); 1.7038(0.50); 1.5642 (0.54); 1.5398 (0.53); 1.2373 (0.48); 1.1925 (0.44);1.1749 (0.77); 1.1571 (0.41); −0.0002 (4.82);

Ex. 5, Solvent: DMSO, Spectrometer: 399.95 MHz

9.2895 (1.04); 8.0347 (0.61); 8.0224 (6.52); 7.4399 (1.29); 7.4356(0.88); 7.4228 (1.56); 7.4191 (1.32); 7.4070 (0.46); 7.4029 (0.38);7.3981 (0.62); 7.3923 (0.44); 7.3782 (1.60); 7.3679 (3.08); 7.3624(5.05); 7.3596 (4.74); 7.3499 (1.29); 7.3461 (0.94); 7.3426 (1.20);7.3366 (0.93); 7.3268 (0.41); 7.3205 (0.35); 6.4907 (3.72); 6.1225(1.00); 6.1019 (1.23); 6.0951 (1.18); 6.0744 (1.01); 5.3418 (0.63);5.2993 (2.10); 5.2489 (2.11); 5.2062 (0.63); 4.3833 (0.64); 4.3517(0.68); 4.0571 (0.33); 4.0393 (0.99); 4.0216 (1.04); 4.0036 (0.56);3.9893 (0.65); 3.9556 (1.68); 3.9278 (1.16); 3.9117 (1.37); 3.8841(1.04); 3.6914 (0.58); 3.4098 (0.54); 3.3999 (0.46); 3.3897 (0.68);3.3809 (1.08); 3.3716 (0.76); 3.3639 (0.87); 3.3518 (0.89); 3.3415(0.94); 3.3111 (259.73); 3.2902 (3.79); 3.2674 (2.30); 3.2469 (1.47);3.2388 (0.80); 3.1410 (0.38); 3.0627 (1.24); 3.0367 (16.00); 2.8689(0.47); 2.8397 (0.83); 2.8127 (0.49); 2.5227 (0.93); 2.5094 (15.18);2.5051 (28.85); 2.5006 (38.17); 2.4962 (26.96); 2.4919 (13.31); 2.2395(0.55); 2.2089 (13.78); 2.1942 (1.10); 2.1356 (0.66); 2.1070 (1.31);2.0692 (0.96); 1.9868 (4.35); 1.8229 (0.53); 1.8181 (0.54); 1.7939(0.54); 1.5861 (0.53); 1.5774 (0.55); 1.5554 (0.54); 1.5469 (0.49);1.1928 (1.19); 1.1750 (2.37); 1.1572 (1.17); −0.0002 (3.61);

Ex. 6, Solvent: DMSO, Spectrometer: 399.95 MHz

9.2891 (0.72); 8.6090 (2.11); 8.0212 (5.44); 7.7010 (1.17); 7.6808(1.36); 7.5331 (1.79); 7.4826 (1.13); 7.4629 (0.95); 7.4392 (0.99);7.4219 (1.32); 7.3812 (0.58); 7.3765 (1.02); 7.3737 (0.84); 7.3657(2.95); 7.3610 (4.08); 7.3486 (1.19); 7.3386 (0.95); 7.3329 (0.62);7.3231 (0.41); 7.3165 (0.33); 7.2175 (1.04); 7.2125 (0.84); 7.0783(2.26); 6.9389 (1.27); 6.1220 (0.82); 6.1014 (1.01); 6.0944 (0.95);6.0738 (0.82); 5.7462 (2.07); 4.1756 (1.13); 4.1420 (1.16); 4.0571(1.24); 4.0392 (3.64); 4.0215 (3.66); 4.0037 (1.25); 3.9569 (0.80);3.9293 (0.95); 3.9132 (1.04); 3.8857 (0.86); 3.3658 (0.95); 3.3562(1.26); 3.3115 (379.65); 3.2929 (3.24); 3.2881 (3.63); 3.2699 (1.15);3.2492 (0.96); 3.0674 (0.78); 3.0335 (14.21); 3.0093 (0.89); 2.6696(0.36); 2.5395 (0.51); 2.5227 (1.67); 2.5094 (21.20); 2.5050 (39.09);2.5006 (50.66); 2.4961 (34.76); 2.4917 (16.36); 2.3273 (0.33); 2.2178(0.36); 2.1093 (0.96); 2.0839 (1.04); 2.0692 (0.85); 1.9868 (16.00);1.7223 (0.39); 1.7017 (0.78); 1.6925 (0.89); 1.6709 (0.81); 1.6622(0.78); 1.6401 (0.32); 1.1928 (4.42); 1.1750 (8.83); 1.1572 (4.29);−0.0002 (3.01);

Ex. 7, Solvent: DMSO, Spectrometer: 399.95 MHz

10.1836 (3.67); 8.0340 (1.04); 8.0300 (1.06); 8.0234 (0.39); 8.0136(1.65); 8.0089 (4.95); 7.7370 (0.43); 7.7337 (0.44); 7.7181 (1.11);7.6992 (0.83); 7.6958 (0.77); 7.6247 (1.02); 7.6151 (1.42); 7.6082(1.43); 7.5965 (0.99); 7.5902 (0.70); 6.4891 (2.20); 6.4455 (0.64);6.4295 (0.73); 6.4178 (0.72); 6.4016 (0.65); 5.3357 (0.39); 5.2934(1.36); 5.2448 (1.33); 5.2022 (0.40); 4.3745 (0.40); 4.3415 (0.42);4.0904 (0.73); 4.0623 (0.98); 4.0582 (1.38); 4.0465 (1.15); 4.0403(3.76); 4.0225 (3.92); 4.0047 (1.32); 3.9801 (0.39); 3.9464 (0.42);3.3867 (0.33); 3.3675 (0.44); 3.3582 (0.71); 3.3486 (0.53); 3.3119(67.25); 3.2901 (1.13); 3.2567 (0.61); 3.2245 (1.14); 3.2083 (0.92);3.1808 (0.82); 3.1646 (0.81); 2.8299 (0.49); 2.5242 (0.45); 2.5109(5.48); 2.5066 (9.98); 2.5022 (12.87); 2.4978 (8.97); 2.4934 (4.35);2.2075 (8.36); 2.1937 (0.49); 2.1142 (0.38); 2.0859 (0.79); 2.0539(0.45); 1.9879 (16.00); 1.8041 (0.33); 1.5593 (0.33); 1.1937 (4.44);1.1759 (8.69); 1.1581 (4.32); −0.0002 (1.14);

Ex. 8, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0325 (7.66); 7.3371 (0.58); 7.3239 (0.66); 7.3135 (1.27); 7.3006(1.28); 7.2903 (0.80); 7.2774 (0.69); 7.1557 (0.88); 7.1517 (0.92);7.1310 (1.53); 7.1282 (1.53); 7.1075 (0.72); 7.1039 (0.75); 6.4985(4.27); 6.0167 (1.08); 5.9957 (1.29); 5.9867 (1.24); 5.9655 (1.13);5.7569 (5.74); 5.3556 (0.89); 5.3130 (2.67); 5.2626 (2.59); 5.2199(0.87); 4.8983 (6.61); 4.8924 (6.85); 4.3934 (0.74); 4.3595 (0.79);4.0554 (0.42); 4.0376 (1.27); 4.0198 (1.32); 4.0018 (0.93); 3.9614(0.79); 3.9404 (0.88); 3.9094 (0.93); 3.8967 (1.11); 3.8666 (0.96);3.6481 (1.57); 3.6423 (3.36); 3.6365 (1.60); 3.5741 (1.15); 3.5528(1.15); 3.5305 (0.96); 3.5096 (0.94); 3.4245 (0.50); 3.4152 (0.35);3.4055 (0.61); 3.3964 (1.06); 3.3870 (0.61); 3.3773 (0.38); 3.3676(0.56); 3.3225 (46.65); 3.3203 (44.06); 3.2718 (1.05); 3.2434 (0.58);2.8715 (0.52); 2.8411 (0.95); 2.8131 (0.55); 2.6702 (0.42); 2.5056(48.88); 2.5012 (65.94); 2.4967 (48.92); 2.3322 (0.35); 2.3279 (0.48);2.3234 (0.37); 2.2090 (16.00); 2.1483 (0.73); 2.1167 (1.47); 2.0843(0.81); 1.9886 (5.44); 1.8305 (0.63); 1.8063 (0.59); 1.5951 (0.59);1.5861 (0.66); 1.5648 (0.62); 1.5551 (0.59); 1.2350 (0.41); 1.1921(1.52); 1.1744 (2.98); 1.1565 (1.49); −0.0002 (0.53);

Ex. 9, Solvent: DMSO, Spectrometer: 601.6 MHz

8.7986 (0.66); 8.0310 (8.32); 7.2995 (0.69); 7.2946 (0.76); 7.2881(0.78); 7.2832 (1.00); 7.2804 (0.82); 7.2719 (1.20); 7.2640 (0.95);7.1948 (0.36); 7.1816 (1.61); 7.1749 (4.74); 7.1700 (3.35); 7.1620(0.57); 6.5053 (4.59); 5.9817 (1.40); 5.9695 (1.56); 5.9631 (1.51);5.9508 (1.40); 5.3490 (1.22); 5.3206 (2.49); 5.2629 (2.73); 5.2345(1.36); 4.8465 (6.64); 4.8425 (6.72); 4.3803 (0.78); 4.3586 (0.79);4.0454 (0.50); 4.0335 (1.51); 4.0217 (1.53); 4.0099 (0.52); 3.9788(0.77); 3.9559 (0.83); 3.9467 (1.50); 3.9279 (1.43); 3.9180 (1.55);3.8993 (1.28); 3.6568 (1.85); 3.6528 (3.82); 3.6489 (1.79); 3.4028(0.55); 3.3968 (0.89); 3.3901 (0.81); 3.3837 (1.25); 3.3774 (2.09);3.3501 (362.44); 3.3314 (3.04); 3.3265 (6.83); 3.3192 (2.05); 3.2812(0.72); 3.2610 (1.14); 3.2424 (0.63); 3.2383 (0.57); 2.8500 (0.59);2.8293 (1.02); 2.8118 (0.58); 2.6180 (0.80); 2.6150 (1.06); 2.6119(0.84); 2.5955 (0.79); 2.5427 (0.99); 2.5242 (3.13); 2.5211 (3.99);2.5180 (4.63); 2.5091 (55.45); 2.5062 (113.82); 2.5032 (153.80); 2.5002(112.48); 2.4973 (52.77); 2.3904 (0.76); 2.3874 (1.01); 2.3844 (0.75);2.2050 (16.00); 2.1921 (0.42); 2.1267 (1.03); 2.1005 (1.11); 2.0964(1.11); 2.0782 (2.13); 1.9905 (6.69); 1.8367 (0.34); 1.8301 (0.39);1.8160 (0.72); 1.8101 (0.76); 1.7955 (0.72); 1.7897 (0.64); 1.5690(0.67); 1.5625 (0.69); 1.5483 (0.68); 1.5424 (0.63); 1.3968 (0.37);1.2335 (0.74); 1.1860 (1.93); 1.1741 (4.07); 1.1623 (2.09); 1.0380(0.32); 1.0270 (0.34); 0.0052 (1.52); −0.0002 (35.42); −0.0058 (1.08);

Ex. 10, Solvent: CDCl3, Spectrometer: 601.6 MHz

7.6273 (0.91); 7.4326 (0.47); 7.3245 (1.12); 7.3113 (2.15); 7.2984(1.22); 7.2614 (79.66); 7.0850 (0.46); 7.0266 (1.81); 7.0149 (3.61);6.9414 (1.96); 6.9281 (1.90); 6.3350 (6.11); 5.7351 (0.78); 5.0298(0.59); 5.0034 (1.60); 4.9737 (1.59); 4.9498 (0.67); 4.7006 (6.62);4.6971 (6.67); 4.5817 (0.75); 4.5629 (0.74); 4.0571 (0.70); 4.0394(0.71); 3.8349 (0.45); 3.8052 (0.32); 3.7893 (0.48); 3.6444 (0.47);3.4187 (0.48); 3.3067 (1.20); 2.9123 (0.46); 2.8936 (0.76); 2.8745(0.47); 2.5105 (2.38); 2.5071 (4.68); 2.5036 (2.42); 2.3239 (16.00);2.2858 (0.44); 2.2145 (0.77); 2.1812 (0.75); 2.1629 (0.73); 1.7957(0.89); 1.7805 (0.92); 1.5858 (3.62); 1.4787 (0.49); 1.4746 (0.46);1.4321 (1.33); 1.4270 (0.89); 1.3860 (0.35); 1.3330 (0.38); 1.2928(0.37); 1.2844 (0.63); 1.2542 (3.05); 0.8801 (0.63); 0.8683 (0.37);0.0695 (1.41); 0.0051 (0.53); −0.0002 (16.59); −0.0057 (0.63);

Ex. 11, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9670 (8.64); 7.4133 (1.85); 7.3924 (3.34); 7.3720 (2.70); 7.1610(3.06); 7.1564 (4.00); 7.1394 (2.50); 7.1365 (3.63); 6.5060 (4.36);6.4950 (0.39); 6.2328 (1.37); 6.2083 (1.80); 6.2020 (1.66); 6.1773(1.43); 5.7627 (11.00); 5.3613 (0.91); 5.3188 (2.57); 5.2700 (2.50);5.2274 (0.88); 5.2032 (0.65); 4.8393 (0.34); 4.8331 (0.35); 4.7990(2.74); 4.7910 (3.74); 4.7843 (2.83); 4.7503 (0.35); 4.7444 (0.36);4.3942 (0.68); 4.3599 (0.74); 4.0366 (0.92); 4.0188 (0.97); 4.0009(0.80); 3.9622 (0.72); 3.7667 (1.02); 3.7357 (1.26); 3.7247 (1.76);3.6937 (1.42); 3.5797 (1.57); 3.5551 (1.60); 3.5376 (1.16); 3.5132(1.16); 3.4596 (1.33); 3.4540 (3.13); 3.4482 (1.65); 3.4179 (0.79);3.3720 (137.80); 3.3689 (145.30); 3.3659 (149.76); 3.3644 (142.87);3.3627 (145.05); 3.3600 (158.31); 3.3560 (182.12); 3.3095 (0.97); 3.3026(0.97); 3.2719 (1.19); 3.2437 (0.75); 3.0425 (1.70); 2.8727 (0.55);2.8540 (1.66); 2.8448 (0.94); 2.8151 (0.55); 2.6774 (0.52); 2.6728(0.75); 2.6682 (0.55); 2.5431 (0.37); 2.5262 (1.22); 2.5215 (1.91);2.5128 (37.79); 2.5083 (83.02); 2.5037 (112.86); 2.4991 (80.19); 2.4945(37.37); 2.3350 (0.54); 2.3304 (0.75); 2.3258 (0.59); 2.2082 (16.00);2.1945 (0.98); 2.1899 (1.51); 2.1522 (0.65); 2.1249 (1.35); 2.0903(0.76); 2.0774 (1.61); 1.9902 (4.31); 1.8271 (0.61); 1.8026 (0.55);1.5943 (0.55); 1.5852 (0.62); 1.5638 (0.59); 1.5543 (0.58); 1.1920(1.20); 1.1742 (2.43); 1.1564 (1.18); 0.0080 (0.86); −0.0002 (29.91);−0.0085 (1.06);

Ex. 12, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9807 (7.00); 7.9525 (2.03); 7.4372 (0.62); 7.4201 (0.81); 7.4161(1.37); 7.3992 (1.36); 7.3953 (0.92); 7.3783 (0.71); 7.0116 (2.03);6.9903 (1.83); 6.9152 (1.03); 6.8897 (1.23); 6.8681 (0.97); 6.5040(3.54); 6.0725 (0.87); 6.0502 (1.06); 6.0421 (1.05); 6.0198 (0.93);5.7619 (3.47); 5.3612 (0.79); 5.3185 (2.23); 5.2681 (2.18); 5.2254(0.77); 5.2021 (0.39); 4.8549 (2.83); 4.8494 (4.94); 4.8440 (2.89);4.3947 (0.60); 4.3602 (0.65); 3.9953 (0.56); 3.9617 (0.63); 3.8129(0.58); 3.7816 (0.67); 3.7697 (0.84); 3.7394 (0.76); 3.5560 (1.45);3.5502 (3.42); 3.5443 (1.54); 3.5246 (1.00); 3.5023 (1.02); 3.4818(0.82); 3.4598 (0.76); 3.4187 (0.44); 3.4089 (0.41); 3.3998 (0.66);3.3913 (1.02); 3.3798 (0.82); 3.3704 (1.02); 3.3457 (545.02); 3.3221(4.34); 3.3102 (1.10); 3.3056 (1.13); 3.3023 (1.08); 3.2853 (0.48);3.2711 (1.05); 3.2430 (0.56); 3.0425 (0.81); 2.8905 (16.00); 2.8710(0.48); 2.8540 (0.86); 2.8400 (0.81); 2.8132 (0.46); 2.7305 (13.08);2.6765 (0.51); 2.6719 (0.75); 2.6675 (0.56); 2.5251 (1.29); 2.5116(41.13); 2.5073 (87.25); 2.5029 (117.49); 2.4984 (86.16); 2.4940(42.72); 2.3339 (0.59); 2.3295 (0.81); 2.3250 (0.63); 2.2085 (13.04);2.1948 (1.13); 2.1521 (0.59); 2.1218 (1.21); 2.0879 (0.69); 2.0769(1.06); 1.8268 (0.53); 1.8037 (0.49); 1.5934 (0.48); 1.5834 (0.56);1.5624 (0.51); 1.5537 (0.50); 1.2342 (0.40); −0.0002 (8.23); −0.0082(0.39);

Ex. 13, Solvent: DMSO, Spectrometer: 399.95 MHz

14.0244 (0.35); 8.7870 (0.54); 8.0352 (0.87); 8.0139 (7.56); 7.9916(0.41); 7.4835 (0.44); 7.3543 (0.48); 7.3427 (0.95); 7.3228 (3.44);7.3042 (2.77); 7.2237 (0.37); 7.1506 (1.98); 7.1313 (1.63); 7.0188(1.03); 7.0022 (2.00); 6.9812 (0.94); 6.4963 (4.60); 6.4409 (0.35);5.8865 (0.96); 5.8680 (1.10); 5.8584 (1.12); 5.8418 (0.94); 5.7554(7.99); 5.3481 (0.81); 5.3051 (2.51); 5.2549 (2.40); 5.2126 (0.97);4.9731 (0.39); 4.8801 (5.11); 4.8742 (5.27); 4.8150 (0.71); 4.3826(0.80); 4.3501 (0.83); 4.0743 (0.38); 4.0556 (0.68); 4.0374 (1.57);4.0200 (1.64); 4.0020 (0.67); 3.9809 (0.75); 3.9478 (1.00); 3.9202(0.45); 3.8988 (1.16); 3.8703 (1.18); 3.8556 (1.32); 3.8277 (1.08);3.6664 (0.48); 3.5857 (1.80); 3.5799 (3.73); 3.5739 (1.64); 3.4875(0.36); 3.4448 (0.36); 3.3987 (0.82); 3.3776 (1.05); 3.3700 (1.49);3.3581 (1.33); 3.3228 (817.78); 3.2695 (1.87); 3.2515 (1.78); 3.2263(1.66); 3.2089 (1.19); 2.8589 (0.68); 2.8302 (1.05); 2.8000 (0.72);2.6750 (1.40); 2.6704 (2.12); 2.6660 (1.35); 2.5407 (1.00); 2.5236(3.21); 2.5096 (115.86); 2.5056 (225.44); 2.5012 (312.93); 2.4970(220.11); 2.4928 (110.70); 2.3323 (1.37); 2.3278 (1.83); 2.3232 (1.36);2.2160 (1.34); 2.2057 (16.00); 2.1935 (1.07); 2.1279 (0.79); 2.0993(1.48); 2.0918 (1.41); 2.0733 (1.50); 2.0630 (0.99); 1.9884 (6.91);1.9085 (0.84); 1.8351 (0.38); 1.8160 (0.73); 1.7837 (0.64); 1.6017(0.35); 1.5716 (0.65); 1.5643 (0.65); 1.5516 (0.49); 1.5420 (0.71);1.5104 (0.36); 1.2338 (0.91); 1.1922 (1.92); 1.1745 (3.72); 1.1567(1.78); −0.0002 (5.87);

Ex. 14, Solvent: DMSO, Spectrometer: 399.95 MHz

8.3198 (0.45); 8.0443 (16.00); 7.6053 (8.46); 7.4479 (2.82); 7.4440(3.38); 7.4289 (3.83); 7.4249 (4.61); 7.4157 (1.89); 7.4115 (1.78);7.3965 (3.75); 7.3921 (3.24); 7.3771 (3.07); 7.3727 (2.56); 7.3116(2.76); 7.3090 (3.00); 7.2927 (4.30); 7.2903 (4.41); 7.2742 (1.69);7.2714 (1.67); 7.1953 (0.33); 7.1890 (0.37); 7.1773 (4.76); 7.1747(4.70); 7.1646 (0.64); 7.1572 (4.19); 7.1547 (3.90); 7.0597 (0.56);7.0538 (0.44); 6.9641 (0.42); 6.9357 (0.32); 5.7610 (2.36); 5.7415(2.76); 5.7327 (2.75); 5.7131 (2.43); 5.6385 (1.87); 5.5956 (4.12);5.5268 (4.32); 5.4837 (1.93); 5.2693 (1.37); 5.1452 (0.97); 4.3548(1.53); 4.3219 (1.65); 4.2712 (0.57); 4.2535 (0.57); 4.1720 (0.81);4.1542 (0.81); 4.0376 (0.50); 4.0198 (0.52); 3.9738 (1.43); 3.9402(1.61); 3.8975 (2.31); 3.8689 (2.63); 3.8543 (2.98); 3.8258 (2.50);3.4591 (6.28); 3.4189 (2.28); 3.4100 (1.64); 3.3991 (1.84); 3.3896(2.54); 3.3804 (1.64); 3.3705 (1.13); 3.3608 (1.37); 3.3524 (0.85);3.3033 (1.33); 3.2908 (3.27); 3.2715 (5.00); 3.2551 (1.06); 3.2475(3.40); 3.2283 (2.80); 2.8827 (1.10); 2.8529 (1.97); 2.8254 (1.12);2.6763 (0.67); 2.6719 (0.93); 2.6674 (0.70); 2.5251 (2.77); 2.5116(51.56); 2.5073 (103.29); 2.5028 (137.32); 2.4983 (103.49); 2.4940(53.38); 2.3383 (0.39); 2.3341 (0.72); 2.3296 (0.98); 2.3250 (0.76);2.1282 (1.37); 2.0962 (2.94); 2.0665 (1.68); 1.9896 (2.19); 1.8721(0.77); 1.8557 (1.68); 1.8402 (2.83); 1.8344 (2.00); 1.8291 (2.06);1.8213 (2.02); 1.8092 (1.64); 1.8011 (1.32); 1.7709 (1.16); 1.7423(0.46); 1.5818 (0.52); 1.5725 (0.61); 1.5514 (1.21); 1.5424 (1.31);1.5208 (1.42); 1.5096 (1.32); 1.5013 (0.75); 1.4976 (0.58); 1.4893(1.15); 1.4832 (0.66); 1.4775 (0.66); 1.4697 (0.52); 1.3973 (6.91);1.3362 (0.81); 1.2837 (0.58); 1.2659 (1.15); 1.2587 (0.35); 1.2486(1.33); 1.2341 (0.81); 1.2155 (0.95); 1.1977 (1.80); 1.1929 (0.73);1.1798 (1.22); 1.1751 (1.33); 1.1611 (0.85); 1.1573 (0.83); 1.1435(0.42); 1.0719 (0.82); 1.0639 (1.00); 1.0562 (1.20); 1.0509 (2.43);1.0454 (3.02); 1.0299 (5.26); 1.0181 (3.59); 1.0131 (5.32); 1.0065(4.05); 1.0009 (2.53); 0.9945 (2.60); 0.9852 (2.73); 0.9784 (2.29);0.9715 (1.96); 0.9603 (2.81); 0.9461 (1.55); 0.9397 (1.46); 0.9268(0.72); 0.9190 (0.42); 0.8188 (0.79); 0.8116 (1.69); 0.8057 (0.80);0.7989 (0.71); 0.7916 (1.70); 0.7858 (1.34); 0.7792 (1.57); 0.7723(1.40); 0.7679 (1.82); 0.7604 (0.79); 0.7031 (0.49); 0.6996 (0.42);0.6916 (0.93); 0.6717 (0.48); 0.1459 (0.40); 0.0080 (3.19); −0.0002(88.57); −0.0083 (4.15); −0.1498 (0.41);

Ex. 15, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0022 (6.06); 7.2119 (2.20); 7.1906 (2.38); 7.0017 (1.16); 6.8645(2.76); 6.7274 (1.32); 6.6819 (2.46); 6.6761 (2.69); 6.5676 (1.45);6.5618 (1.32); 6.5464 (1.38); 6.5405 (1.27); 6.2950 (2.93); 5.8001(0.91); 5.7812 (1.08); 5.7726 (1.04); 5.7536 (0.91); 5.2633 (0.66);5.2211 (2.00); 5.1739 (1.99); 5.1317 (0.66); 4.7914 (3.28); 4.7856(3.33); 4.3874 (0.60); 4.3555 (0.64); 4.0550 (0.61); 4.0372 (1.88);4.0194 (2.07); 4.0016 (1.16); 3.9720 (0.63); 3.8129 (0.51); 3.8030(0.90); 3.7752 (1.07); 3.7601 (1.52); 3.7498 (16.00); 3.7327 (1.19);3.3994 (0.46); 3.3898 (0.41); 3.3804 (0.62); 3.3705 (1.06); 3.3443(19.58); 3.2887 (1.45); 3.2698 (1.23); 3.2462 (1.44); 3.2269 (1.21);2.8478 (0.42); 2.8168 (0.73); 2.7894 (0.42); 2.6759 (0.35); 2.6714(0.50); 2.6667 (0.36); 2.5246 (1.35); 2.5111 (28.23); 2.5067 (57.28);2.5022 (77.36); 2.4977 (59.44); 2.4933 (31.35); 2.3335 (0.45); 2.3290(0.59); 2.3246 (0.45); 2.1850 (11.90); 2.1215 (0.63); 2.0914 (1.22);2.0625 (0.73); 1.9894 (8.21); 1.9090 (6.30); 1.8492 (0.43); 1.8437(0.49); 1.8203 (4.10); 1.8147 (8.12); 1.8090 (4.37); 1.7947 (0.89);1.7870 (0.79); 1.7650 (0.65); 1.7334 (0.36); 1.7090 (0.40); 1.5650(0.52); 1.5556 (0.57); 1.5342 (0.54); 1.5248 (0.51); 1.3972 (4.83);1.1924 (2.19); 1.1746 (4.35); 1.1568 (2.16); −0.0002 (4.21);

Ex. 16, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0006 (2.31); 7.6034 (1.53); 7.2960 (0.90); 7.2769 (1.11); 7.2613(0.46); 7.0222 (0.79); 7.0014 (0.64); 6.9487 (0.48); 6.9297 (0.81);6.9115 (0.38); 5.8714 (0.37); 5.8527 (0.45); 5.8428 (0.41); 5.8247(0.38); 5.6335 (0.34); 5.5902 (0.75); 5.5240 (0.77); 5.4812 (0.35);4.0375 (0.46); 4.0198 (0.47); 3.9353 (0.34); 3.9227 (0.42); 3.9055(0.37); 3.8967 (0.66); 3.8798 (0.68); 3.8683 (0.49); 3.8608 (0.68);3.8417 (0.85); 3.8254 (0.59); 3.8173 (0.39); 3.7974 (0.51); 3.3817(0.40); 3.3519 (0.84); 3.3277 (40.80); 3.3089 (0.72); 3.2908 (0.55);3.2726 (0.39); 2.8544 (0.37); 2.5065 (34.94); 2.5021 (44.66); 2.4978(32.56); 2.0951 (0.53); 1.9892 (1.91); 1.7901 (0.47); 1.3975 (16.00);1.1926 (0.65); 1.1748 (1.22); 1.1635 (0.38); 1.1569 (0.69); 0.4971(0.47); 0.4926 (0.48); 0.4770 (0.35); 0.4719 (0.39); 0.4383 (0.41);0.4355 (0.42); 0.4156 (0.53); 0.3161 (0.39); 0.3042 (1.21); 0.2920(1.16); 0.2798 (0.33); 0.0074 (0.34); −0.0002 (6.70);

Ex. 17, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9983 (5.82); 7.2945 (1.82); 7.2899 (1.35); 7.2782 (2.10); 7.2749(2.41); 7.2605 (1.12); 7.2564 (0.65); 7.0215 (1.85); 7.0012 (1.44);6.9475 (1.09); 6.9288 (1.88); 6.9100 (0.90); 6.4963 (3.32); 5.8720(0.89); 5.8540 (1.03); 5.8439 (1.00); 5.8256 (0.91); 5.3524 (0.74);5.3099 (2.04); 5.2561 (2.05); 5.2139 (0.74); 4.3815 (0.61); 4.3486(0.65); 4.0554 (1.24); 4.0376 (3.73); 4.0198 (3.80); 4.0020 (1.38);3.9778 (0.62); 3.9512 (0.66); 3.9230 (0.77); 3.9060 (0.81); 3.8974(1.53); 3.8805 (1.59); 3.8675 (1.14); 3.8613 (1.62); 3.8436 (1.73);3.8396 (1.60); 3.8247 (1.40); 3.8181 (0.87); 3.7966 (1.17); 3.4009(0.48); 3.3909 (0.41); 3.3814 (0.57); 3.3722 (0.95); 3.3627 (0.70);3.3497 (1.79); 3.3276 (79.63); 3.3070 (1.34); 3.2891 (1.39); 3.2626(0.80); 3.2345 (0.46); 2.8634 (0.46); 2.8364 (0.77); 2.8052 (0.44);2.6755 (0.35); 2.6711 (0.48); 2.6666 (0.37); 2.5413 (0.36); 2.5242(1.94); 2.5109 (26.73); 2.5066 (52.99); 2.5020 (70.08); 2.4975 (51.35);2.4931 (24.86); 2.3334 (0.36); 2.3287 (0.49); 2.3242 (0.35); 2.2060(12.17); 2.1946 (1.38); 2.1218 (0.64); 2.0943 (1.15); 2.0628 (0.65);1.9889 (16.00); 1.8140 (0.48); 1.8048 (0.53); 1.7901 (0.65); 1.7831(0.48); 1.7735 (0.44); 1.5719 (0.45); 1.5629 (0.48); 1.5414 (0.44);1.3975 (3.38); 1.2981 (0.32); 1.2585 (0.46); 1.1928 (4.73); 1.1823(0.70); 1.1750 (9.35); 1.1655 (0.93); 1.1572 (4.79); 1.1484 (0.55);0.5290 (0.41); 0.5213 (0.46); 0.5172 (0.45); 0.5093 (0.62); 0.5002(1.09); 0.4953 (1.09); 0.4799 (0.79); 0.4747 (0.87); 0.4435 (0.90);0.4399 (0.93); 0.4232 (1.00); 0.4197 (1.14); 0.4111 (0.52); 0.3980(0.53); 0.3912 (0.48); 0.3410 (0.34); 0.3288 (0.49); 0.3178 (0.85);0.3058 (2.78); 0.2987 (1.55); 0.2937 (2.71); 0.2884 (0.99); 0.2816(0.72); 0.2705 (0.33); 0.0079 (0.51); −0.0002 (13.14); −0.0084 (0.45);

Ex. 18, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0100 (7.83); 7.3118 (1.40); 7.3083 (1.78); 7.3041 (1.62); 7.2943(2.33); 7.2897 (2.40); 7.2853 (1.75); 7.2763 (1.44); 7.2721 (0.74);7.2072 (1.33); 7.0725 (3.05); 7.0619 (2.31); 7.0512 (0.40); 7.0415(1.80); 6.9747 (1.29); 6.9548 (2.22); 6.9378 (2.47); 6.3833 (3.14);6.0804 (0.38); 6.0679 (0.83); 6.0545 (0.62); 6.0414 (0.95); 6.0372(0.50); 6.0289 (0.50); 6.0246 (1.01); 6.0117 (0.70); 5.9981 (1.01);5.9857 (0.48); 5.9181 (1.13); 5.9002 (1.30); 5.8903 (1.27); 5.8723(1.15); 5.7570 (3.27); 5.4432 (0.61); 5.4389 (1.72); 5.4346 (1.75);5.4303 (0.63); 5.3999 (0.53); 5.3956 (1.50); 5.3913 (1.52); 5.3870(0.54); 5.2461 (1.93); 5.2421 (2.23); 5.2232 (0.68); 5.2196 (1.65);5.2156 (1.65); 5.2119 (0.72); 5.1988 (2.50); 5.1594 (2.44); 5.1170(0.61); 4.6326 (2.29); 4.6277 (2.51); 4.6207 (2.41); 4.6155 (2.15);4.3629 (0.64); 4.3301 (0.66); 4.0380 (0.34); 4.0201 (0.36); 4.0020(0.38); 3.9912 (0.60); 3.9560 (0.65); 3.8912 (1.23); 3.8632 (1.40);3.8483 (1.59); 3.8205 (1.34); 3.3920 (0.47); 3.3822 (0.34); 3.3726(0.57); 3.3633 (1.01); 3.3540 (0.59); 3.3439 (0.40); 3.3344 (0.69);3.3217 (20.52); 3.2980 (1.00); 3.2864 (1.56); 3.2684 (1.90); 3.2434(1.82); 3.2358 (0.93); 3.2257 (1.60); 3.2068 (0.46); 2.8344 (0.45);2.8070 (0.80); 2.7767 (0.45); 2.5239 (0.38); 2.5104 (8.89); 2.5060(18.38); 2.5015 (24.50); 2.4969 (17.47); 2.4925 (8.24); 2.1608 (16.00);2.1069 (0.59); 2.0769 (1.25); 2.0475 (0.69); 1.9888 (1.44); 1.7741(0.52); 1.7658 (0.56); 1.7431 (0.51); 1.7356 (0.48); 1.5590 (0.50);1.5502 (0.54); 1.5283 (0.51); 1.5194 (0.49); 1.1923 (0.40); 1.1745(0.79); 1.1567 (0.39); −0.0002 (2.77);

Ex. 19, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0312 (8.75); 7.2693 (0.58); 7.2561 (0.65); 7.2458 (1.28); 7.2329(1.27); 7.2224 (0.79); 7.2095 (0.70); 7.1053 (0.91); 7.1011 (0.94);7.0806 (1.50); 7.0776 (1.46); 7.0573 (0.72); 7.0529 (0.72); 6.4986(4.24); 6.0692 (0.43); 6.0559 (0.90); 6.0428 (0.88); 6.0295 (1.08);6.0261 (0.60); 6.0129 (2.13); 5.9996 (1.15); 5.9927 (1.37); 5.9862(1.78); 5.9732 (0.64); 5.9624 (1.15); 5.7570 (0.58); 5.4267 (0.69);5.4226 (1.94); 5.4184 (1.98); 5.4144 (0.73); 5.3836 (0.61); 5.3795(1.70); 5.3752 (1.75); 5.3711 (0.66); 5.3554 (0.86); 5.3128 (2.63);5.2955 (0.92); 5.2922 (1.94); 5.2882 (1.83); 5.2621 (4.13); 5.2201(0.87); 4.6447 (2.44); 4.6414 (4.03); 4.6380 (2.54); 4.6315 (2.56);4.6281 (3.94); 4.6248 (2.36); 4.3925 (0.70); 4.3596 (0.74); 4.0555(0.72); 4.0377 (2.18); 4.0199 (2.24); 4.0020 (1.21); 3.9612 (0.74);3.9377 (0.84); 3.9073 (0.91); 3.8944 (1.09); 3.8642 (0.96); 3.5677(3.27); 3.5469 (1.17); 3.5247 (0.95); 3.5037 (0.94); 3.4241 (0.52);3.4148 (0.36); 3.4049 (0.61); 3.3955 (1.10); 3.3863 (0.63); 3.3760(0.41); 3.3667 (0.58); 3.3573 (0.34); 3.3203 (81.65); 3.2966 (3.58);3.2716 (0.97); 3.2433 (0.53); 3.0430 (0.53); 2.8705 (0.50); 2.8545(0.64); 2.8441 (0.89); 2.8134 (0.52); 2.6748 (0.40); 2.6703 (0.56);2.6657 (0.41); 2.5237 (1.15); 2.5102 (29.77); 2.5058 (61.50); 2.5012(81.81); 2.4966 (58.12); 2.4922 (27.28); 2.3328 (0.40); 2.3279 (0.56);2.3233 (0.41); 2.2095 (16.00); 2.1930 (0.82); 2.1485 (0.67); 2.1195(1.36); 2.0862 (0.74); 1.9886 (9.64); 1.8292 (0.58); 1.8061 (0.53);1.5944 (0.55); 1.5857 (0.61); 1.5651 (0.56); 1.5559 (0.55); 1.3975(1.01); 1.1922 (2.65); 1.1744 (5.35); 1.1566 (2.61); −0.0002 (8.47);

Ex. 20, Solvent: DMSO, Spectrometer: 601.6 MHz

8.0151 (9.12); 7.3155 (3.02); 7.3017 (3.39); 7.2357 (3.79); 7.2325(3.96); 7.0807 (2.16); 7.0775 (2.10); 7.0671 (1.98); 7.0639 (1.94);6.9503 (1.30); 6.8591 (3.31); 6.7680 (1.51); 6.2923 (3.51); 5.8374(1.29); 5.8259 (1.41); 5.8191 (1.38); 5.8074 (1.30); 5.7541 (10.11);5.2465 (1.00); 5.2183 (2.32); 5.1637 (2.28); 5.1354 (0.99); 4.9420(6.32); 4.9380 (6.43); 4.3777 (0.68); 4.3555 (0.71); 4.0469 (0.32);4.0350 (1.02); 4.0232 (1.03); 4.0113 (0.38); 3.9959 (0.64); 3.9729(0.69); 3.8884 (1.32); 3.8699 (1.56); 3.8599 (1.67); 3.8414 (1.38);3.6384 (1.82); 3.6345 (4.09); 3.6305 (1.81); 3.3844 (0.56); 3.3781(0.34); 3.3717 (0.62); 3.3654 (1.17); 3.3590 (0.65); 3.3526 (0.40);3.3463 (0.61); 3.3401 (0.36); 3.3188 (83.66); 3.2697 (0.51); 3.2545(2.10); 3.2430 (1.81); 3.2303 (0.59); 3.2261 (1.89); 3.2145 (1.53);2.8372 (0.48); 2.8168 (0.86); 2.7989 (0.49); 2.6162 (0.34); 2.6131(0.51); 2.6102 (0.37); 2.5224 (0.87); 2.5194 (1.10); 2.5163 (1.02);2.5074 (23.48); 2.5044 (53.22); 2.5014 (75.43); 2.4984 (54.67); 2.4954(25.33); 2.3887 (0.34); 2.3856 (0.49); 2.3826 (0.36); 2.1853 (16.00);2.1700 (0.43); 2.1154 (0.59); 2.0879 (0.88); 2.0601 (0.65); 1.9884(4.41); 1.7835 (0.53); 1.7779 (0.58); 1.7633 (0.55); 1.7572 (0.54);1.5559 (0.55); 1.5496 (0.60); 1.5358 (0.57); 1.5295 (0.54); 1.3359(0.43); 1.2588 (0.34); 1.2497 (0.56); 1.1870 (1.23); 1.1751 (2.46);1.1633 (1.19); 0.0052 (1.80); −0.0002 (65.36); −0.0058 (2.16);

Ex. 21, Solvent: DMSO, Spectrometer: 399.95 MHz

8.3164 (0.44); 7.9600 (8.55); 7.3175 (3.41); 7.3128 (4.35); 7.2756(4.09); 7.2709 (3.55); 7.0001 (1.52); 6.8629 (3.61); 6.7258 (1.69);6.2950 (3.72); 6.1875 (1.31); 6.1633 (1.68); 6.1568 (1.59); 6.1324(1.36); 5.7567 (11.60); 5.2624 (0.81); 5.2202 (2.75); 5.1767 (2.65);5.1344 (0.80); 4.8983 (0.34); 4.8920 (0.36); 4.8581 (2.93); 4.8500(3.96); 4.8434 (2.94); 4.8094 (0.35); 4.8036 (0.37); 4.3907 (0.77);4.3577 (0.81); 4.0374 (0.66); 4.0195 (1.15); 4.0022 (0.65); 3.9783(0.79); 3.7710 (1.02); 3.7399 (1.26); 3.7287 (1.71); 3.6977 (1.38);3.5613 (1.55); 3.5370 (1.55); 3.5191 (1.13); 3.4949 (1.14); 3.4743(1.69); 3.4685 (3.90); 3.4627 (1.72); 3.4108 (0.56); 3.4015 (0.45);3.3911 (0.69); 3.3820 (1.22); 3.3725 (0.78); 3.3628 (0.64); 3.3258(206.04); 3.3006 (0.81); 3.2947 (0.77); 3.2641 (1.06); 3.2355 (0.57);2.8630 (0.55); 2.8332 (0.98); 2.8054 (0.54); 2.6753 (0.82); 2.6708(1.17); 2.6663 (0.88); 2.5236 (6.05); 2.5106 (61.29); 2.5062 (121.93);2.5017 (162.84); 2.4972 (123.45); 2.4930 (63.26); 2.3374 (0.43); 2.3329(0.86); 2.3285 (1.16); 2.3240 (0.88); 2.1878 (16.00); 2.1455 (0.75);2.1151 (1.49); 2.0825 (0.81); 1.9887 (2.69); 1.7973 (0.64); 1.7738(0.59); 1.5841 (0.59); 1.5759 (0.65); 1.5544 (0.62); 1.5458 (0.58);1.3354 (0.34); 1.2981 (0.40); 1.2586 (0.57); 1.2493 (0.45); 1.2332(0.51); 1.1925 (0.74); 1.1747 (1.43); 1.1569 (0.71); 0.1460 (0.49);0.0159 (0.96); 0.0079 (4.30); −0.0002 (106.55); −0.0083 (4.46); −0.1498(0.50);

Ex. 22, Solvent: DMSO, Spectrometer: 601.6 MHz

8.3142 (0.34); 7.9946 (7.84); 7.1678 (2.89); 7.1549 (3.09); 6.9506(1.27); 6.8763 (3.42); 6.8594 (3.09); 6.7684 (3.08); 6.7568 (1.77);6.2920 (3.60); 6.0513 (0.42); 6.0431 (0.92); 6.0340 (0.71); 6.0254(0.99); 6.0226 (0.56); 6.0170 (0.53); 6.0143 (1.04); 6.0053 (0.74);5.9966 (1.03); 5.9884 (0.49); 5.8617 (1.21); 5.8495 (1.34); 5.8433(1.28); 5.8310 (1.21); 5.7546 (5.26); 5.4194 (0.67); 5.4167 (1.81);5.4138 (1.84); 5.4110 (0.69); 5.3879 (1.61); 5.3850 (1.63); 5.3822(0.61); 5.2475 (1.04); 5.2255 (1.92); 5.2228 (2.29); 5.2197 (2.66);5.2079 (1.69); 5.2053 (1.70); 5.1630 (2.28); 5.1348 (1.00); 4.6045(1.74); 4.5967 (3.07); 4.5888 (1.72); 4.5750 (0.34); 4.3765 (0.70);4.3542 (0.74); 4.0348 (0.33); 4.0230 (0.35); 3.9958 (0.66); 3.9733(0.72); 3.8315 (1.31); 3.8130 (1.54); 3.8032 (1.64); 3.7847 (1.38);3.7377 (0.60); 3.3858 (0.59); 3.3795 (0.38); 3.3729 (0.67); 3.3666(1.18); 3.3605 (0.69); 3.3536 (0.45); 3.3475 (0.71); 3.3222 (44.05);3.3190 (116.77); 3.2722 (0.53); 3.2596 (1.82); 3.2475 (2.02); 3.2313(1.88); 3.2191 (1.46); 2.8397 (0.50); 2.8194 (0.91); 2.8017 (0.50);2.6159 (0.57); 2.6129 (0.82); 2.6098 (0.57); 2.5222 (1.54); 2.5191(1.95); 2.5160 (1.99); 2.5071 (40.12); 2.5042 (87.09); 2.5011 (121.31);2.4981 (87.79); 2.4951 (40.80); 2.3885 (0.58); 2.3853 (0.79); 2.3822(0.55); 2.2873 (14.22); 2.1847 (16.00); 2.1701 (0.64); 2.1169 (0.68);2.0884 (0.99); 2.0612 (0.69); 1.9883 (1.39); 1.7829 (0.56); 1.7775(0.60); 1.7631 (0.57); 1.7575 (0.52); 1.5568 (0.55); 1.5504 (0.59);1.5360 (0.55); 1.5300 (0.54); 1.2586 (0.33); 1.2494 (0.42); 1.2351(0.37); 1.1867 (0.40); 1.1748 (0.77); 1.1630 (0.39); 1.1387 (0.54);0.0840 (0.56); 0.0704 (0.41); 0.0052 (0.60); −0.0002 (18.89); −0.0057(0.67);

Ex. 23, Solvent: DMSO, Spectrometer: 600.13 MHz

8.3129 (0.35); 7.9980 (8.12); 7.1849 (2.82); 7.1720 (3.04); 6.9642(3.46); 6.9516 (1.32); 6.8602 (3.12); 6.8177 (1.81); 6.8048 (1.77);6.7688 (1.43); 6.2935 (3.75); 5.8333 (1.17); 5.8212 (1.30); 5.8150(1.26); 5.8027 (1.20); 5.7541 (9.04); 5.2463 (0.99); 5.2179 (2.31);5.1632 (2.30); 5.1350 (1.00); 4.8484 (6.15); 4.8445 (6.19); 4.3766(0.70); 4.3548 (0.73); 4.0350 (0.63); 4.0232 (0.64); 3.9961 (0.66);3.9727 (0.71); 3.8409 (1.23); 3.8224 (1.43); 3.8124 (1.51); 3.7940(1.30); 3.5695 (1.85); 3.5656 (3.91); 3.5617 (1.77); 3.3964 (0.35);3.3923 (0.56); 3.3852 (0.84); 3.3793 (0.75); 3.3719 (1.08); 3.3667(1.90); 3.3611 (1.61); 3.3534 (2.07); 3.3324 (1876.28); 3.3130 (1.81);3.3099 (1.34); 3.3001 (0.44); 3.2903 (0.39); 3.2756 (0.58); 3.2711(0.58); 3.2515 (1.06); 3.2438 (1.67); 3.2315 (2.00); 3.2152 (1.45);3.2031 (1.41); 2.8391 (0.48); 2.8184 (0.91); 2.8009 (0.50); 2.6199(0.75); 2.6170 (1.59); 2.6140 (2.18); 2.6110 (1.56); 2.6080 (0.72);2.5412 (0.38); 2.5230 (3.90); 2.5199 (4.77); 2.5168 (4.61); 2.5079(123.47); 2.5050 (264.64); 2.5019 (362.99); 2.4989 (259.62); 2.4960(118.63); 2.3888 (1.53); 2.3858 (2.11); 2.3828 (1.48); 2.3007 (13.79);2.1852 (16.00); 2.1711 (0.66); 2.1187 (0.61); 2.0909 (0.94); 2.0644(0.69); 1.9885 (2.71); 1.7854 (0.55); 1.7792 (0.58); 1.7644 (0.57);1.7587 (0.53); 1.5569 (0.56); 1.5507 (0.61); 1.5363 (0.57); 1.5305(0.56); 1.3354 (0.58); 1.2981 (0.40); 1.2586 (0.54); 1.2494 (0.71);1.1867 (0.75); 1.1748 (1.46); 1.1630 (0.72); 0.0969 (0.58); 0.0053(4.51); −0.0001 (144.35); −0.0057 (4.44); −0.1002 (0.61);

Ex. 24, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9487 (9.14); 7.2585 (3.72); 7.2537 (4.34); 7.2009 (3.95); 7.1961(3.40); 7.0001 (1.54); 6.8629 (3.75); 6.7258 (1.74); 6.2956 (3.55);6.2149 (1.35); 6.1918 (1.71); 6.1839 (1.57); 6.1607 (1.42); 5.7985(0.35); 5.7847 (0.74); 5.7717 (0.69); 5.7574 (14.11); 5.7415 (0.99);5.7283 (0.83); 5.7152 (0.96); 5.7015 (0.48); 5.2670 (1.27); 5.2629(2.06); 5.2589 (1.98); 5.2552 (0.77); 5.2269 (2.61); 5.2196 (1.95);5.2156 (1.76); 5.2119 (0.71); 5.1747 (2.44); 5.1324 (0.84); 5.0184(1.75); 5.0150 (1.72); 4.9921 (1.62); 4.9887 (1.61); 4.6251 (0.50);4.6117 (0.52); 4.5934 (1.42); 4.5800 (1.39); 4.5623 (1.42); 4.5481(1.38); 4.5305 (0.54); 4.5162 (0.50); 4.3903 (0.70); 4.3565 (0.74);4.0375 (0.76); 4.0196 (1.20); 4.0021 (0.60); 3.9793 (0.72); 3.7660(1.06); 3.7348 (1.32); 3.7238 (1.78); 3.6927 (1.43); 3.5552 (1.55);3.5320 (1.56); 3.5130 (1.14); 3.4899 (1.13); 3.4182 (0.50); 3.4088(0.34); 3.3989 (0.59); 3.3896 (1.07); 3.3802 (0.60); 3.3707 (0.38);3.3608 (0.60); 3.3509 (0.37); 3.3264 (87.67); 3.2992 (0.64); 3.2682(0.96); 3.2394 (0.52); 2.8672 (0.49); 2.8375 (0.88); 2.8104 (0.50);2.6753 (0.41); 2.6707 (0.57); 2.6662 (0.41); 2.5242 (1.47); 2.5193(2.32); 2.5108 (31.82); 2.5063 (63.80); 2.5017 (83.72); 2.4971 (60.62);2.4926 (28.73); 2.3331 (0.43); 2.3285 (0.59); 2.3238 (0.42); 2.1880(16.00); 2.1385 (0.65); 2.1047 (1.35); 2.0757 (0.75); 1.9889 (3.17);1.8040 (0.56); 1.7956 (0.60); 1.7732 (0.58); 1.7656 (0.53); 1.5815(0.56); 1.5726 (0.61); 1.5505 (0.58); 1.5420 (0.56); 1.3356 (0.49);1.2584 (0.42); 1.2492 (0.63); 1.2338 (0.37); 1.1924 (0.89); 1.1746(1.72); 1.1568 (0.85); 1.1382 (0.62); 0.0079 (1.93); −0.0002 (59.95);−0.0085 (1.93);

Ex. 25, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0279 (3.87); 7.9601 (9.47); 7.3975 (0.92); 7.3802 (1.19); 7.3765(1.97); 7.3594 (2.01); 7.3557 (1.30); 7.3385 (1.02); 7.0489 (2.67);7.0297 (3.22); 6.9979 (3.52); 6.9363 (2.80); 6.9151 (2.60); 6.8606(2.26); 6.8413 (3.43); 6.8191 (1.39); 6.1066 (1.31); 6.0846 (1.60);6.0760 (1.51); 6.0540 (1.37); 5.9311 (0.45); 5.9178 (0.95); 5.9047(0.93); 5.8915 (1.12); 5.8882 (0.67); 5.8782 (0.65); 5.8747 (1.25);5.8615 (1.08); 5.8482 (1.20); 5.8352 (0.57); 5.7593 (6.99); 5.3448(0.79); 5.3410 (2.09); 5.3369 (2.15); 5.3330 (0.85); 5.2977 (1.81);5.2936 (1.86); 5.2898 (0.74); 5.1204 (2.05); 5.1168 (2.04); 5.0941(1.91); 5.0904 (1.92); 4.6232 (0.44); 4.6102 (0.41); 4.5907 (2.08);4.5780 (3.26); 4.5707 (1.59); 4.5669 (1.99); 4.5480 (0.36); 4.5344(0.33); 4.1790 (1.94); 4.1451 (2.08); 4.1246 (0.54); 4.1109 (1.03);4.1069 (0.47); 4.0195 (0.32); 3.8018 (0.92); 3.7708 (1.07); 3.7589(1.35); 3.7289 (1.23); 3.5378 (1.52); 3.5157 (1.59); 3.5033 (0.37);3.4946 (1.62); 3.4734 (1.16); 3.3594 (0.67); 3.3299 (55.60); 3.3119(0.73); 3.3021 (0.80); 3.2932 (0.41); 3.0164 (1.33); 2.9868 (2.49);2.9582 (1.39); 2.6708 (0.39); 2.5240 (1.44); 2.5105 (23.49); 2.5062(46.51); 2.5017 (60.90); 2.4971 (44.34); 2.4928 (21.71); 2.3331 (0.33);2.3284 (0.42); 2.3240 (0.32); 2.2329 (16.00); 2.1107 (15.92); 2.0623(1.95); 1.9891 (1.38); 1.7104 (0.55); 1.7005 (0.69); 1.6794 (1.45);1.6707 (1.63); 1.6485 (1.53); 1.6407 (1.42); 1.6187 (0.63); 1.6094(0.50); 1.2152 (0.41); 1.1974 (0.79); 1.1920 (0.42); 1.1795 (0.40);1.1742 (0.75); 1.1564 (0.39); 1.0734 (0.43); 1.0561 (0.43); −0.0002(1.81);

Ex. 26, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0044 (8.17); 7.1884 (2.93); 7.1691 (3.29); 6.9645 (3.82); 6.8199(2.03); 6.8005 (1.84); 6.4986 (4.42); 5.8416 (1.17); 5.8235 (1.36);5.8141 (1.34); 5.7957 (1.22); 5.7589 (1.32); 5.3524 (0.97); 5.3098(2.81); 5.2586 (2.78); 5.2160 (0.98); 4.8515 (6.30); 4.8457 (6.52);4.3839 (0.79); 4.3506 (0.83); 4.0554 (0.99); 4.0376 (3.04); 4.0198(3.09); 4.0020 (1.13); 3.9834 (0.74); 3.9487 (0.81); 3.8553 (1.21);3.8275 (1.40); 3.8124 (1.59); 3.7847 (1.32); 3.5799 (1.54); 3.5741(3.36); 3.5683 (1.55); 3.3983 (0.53); 3.3890 (0.37); 3.3788 (0.65);3.3696 (1.11); 3.3605 (0.68); 3.3502 (0.45); 3.3406 (0.78); 3.3264(27.97); 3.3027 (1.83); 3.2875 (0.62); 3.2541 (2.36); 3.2356 (1.71);3.2111 (1.44); 3.1929 (1.37); 2.8556 (0.60); 2.8258 (0.99); 2.7983(0.57); 2.5240 (0.54); 2.5104 (14.51); 2.5061 (30.55); 2.5016 (42.55);2.4972 (32.69); 2.4931 (16.62); 2.3331 (0.34); 2.3283 (0.36); 2.3001(13.88); 2.2054 (16.00); 2.1934 (1.03); 2.1257 (0.70); 2.0918 (1.50);2.0643 (0.82); 1.9891 (12.98); 1.8182 (0.63); 1.8094 (0.68); 1.7873(0.62); 1.7788 (0.58); 1.5707 (0.60); 1.5614 (0.67); 1.5404 (0.63);1.5310 (0.61); 1.3972 (0.35); 1.2582 (0.37); 1.1922 (3.50); 1.1744(6.96); 1.1566 (3.45); 0.0080 (0.98); −0.0002 (31.85); −0.0084 (1.34);

Ex. 27, Solvent: DMSO, Spectrometer: 600.13 MHz

7.9752 (5.68); 7.1878 (2.27); 7.1737 (2.38); 6.9533 (0.98); 6.8618(2.31); 6.7705 (1.08); 6.5563 (2.43); 6.5524 (2.73); 6.5035 (1.49);6.4997 (1.31); 6.4895 (1.43); 6.4856 (1.29); 6.2946 (2.97); 5.7876(0.95); 5.7750 (1.07); 5.7689 (1.05); 5.7561 (0.99); 5.2512 (0.82);5.2229 (1.82); 5.1646 (1.72); 5.1363 (0.80); 4.3757 (0.58); 4.3538(0.62); 4.0472 (0.33); 4.0353 (0.98); 4.0234 (1.01); 4.0115 (0.42);3.9985 (0.58); 3.9781 (0.66); 3.8896 (0.83); 3.8784 (0.88); 3.8726(1.31); 3.8614 (1.28); 3.8251 (0.53); 3.8178 (1.20); 3.8059 (1.26);3.8008 (0.88); 3.7889 (0.83); 3.7765 (0.42); 3.7713 (0.94); 3.7523(1.13); 3.7426 (2.44); 3.7381 (16.00); 3.7241 (1.06); 3.3894 (0.46);3.3831 (0.34); 3.3766 (0.55); 3.3703 (0.93); 3.3640 (0.57); 3.3550(1.29); 3.3423 (1.27); 3.3254 (75.46); 3.3141 (1.28); 3.2785 (0.47);3.2587 (0.83); 3.2393 (0.45); 2.8902 (2.01); 2.8476 (0.43); 2.8276(0.75); 2.8094 (0.44); 2.7313 (1.69); 2.5226 (0.40); 2.5196 (0.50);2.5164 (0.55); 2.5046 (24.76); 2.5016 (33.47); 2.4987 (24.64); 2.1971(0.62); 2.1869 (11.90); 2.1769 (0.73); 2.1141 (0.58); 2.0870 (0.88);2.0616 (0.61); 1.9888 (4.15); 1.7792 (0.49); 1.7767 (0.49); 1.7618(0.46); 1.7564 (0.43); 1.5543 (0.49); 1.5344 (0.46); 1.3971 (1.43);1.1867 (1.12); 1.1748 (2.20); 1.1629 (1.09); 1.1303 (0.48); 1.1266(0.45); 1.1186 (0.74); 1.1106 (0.48); 1.1069 (0.50); 0.4787 (0.33);0.4766 (0.35); 0.4704 (0.57); 0.4684 (0.53); 0.4629 (0.74); 0.4573(0.64); 0.4508 (0.44); 0.4483 (0.49); 0.4445 (0.38); 0.3860 (0.37);0.3824 (0.50); 0.3806 (0.50); 0.3766 (0.47); 0.3735 (0.54); 0.3672(0.75); 0.3604 (0.58); 0.3524 (0.38); 0.3467 (0.37); 0.2926 (0.41);0.2853 (0.67); 0.2771 (1.19); 0.2721 (1.47); 0.2688 (1.34); 0.2649(1.55); 0.2602 (1.06); 0.2519 (0.61); 0.2448 (0.36); 0.0053 (0.32);−0.0001 (7.89);

Ex. 28, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9638 (7.36); 7.3700 (0.76); 7.3492 (1.67); 7.3319 (1.71); 7.3111(0.82); 7.0001 (1.52); 6.8633 (4.36); 6.8462 (2.41); 6.8378 (1.50);6.8131 (1.71); 6.7911 (1.22); 6.7259 (1.68); 6.2950 (3.99); 6.0878(1.17); 6.0666 (1.43); 6.0570 (1.34); 6.0360 (1.20); 5.2707 (0.96);5.2284 (2.60); 5.1725 (2.60); 5.1300 (0.96); 4.3861 (0.85); 4.3540(0.91); 4.0552 (0.55); 4.0373 (1.66); 4.0195 (2.13); 4.0018 (1.14);3.9758 (0.92); 3.9028 (1.21); 3.8858 (1.35); 3.8773 (1.72); 3.8606(1.63); 3.7919 (0.92); 3.7547 (1.94); 3.7504 (1.87); 3.7364 (1.68);3.7301 (1.42); 3.7187 (1.47); 3.7115 (1.31); 3.6042 (1.39); 3.5831(1.39); 3.5620 (0.94); 3.5412 (1.00); 3.4136 (0.63); 3.4040 (0.49);3.3938 (0.78); 3.3847 (1.22); 3.3754 (0.83); 3.3650 (0.65); 3.3556(0.93); 3.3272 (76.50); 3.3019 (0.92); 3.2641 (1.16); 3.2353 (0.64);2.8622 (0.60); 2.8337 (1.08); 2.8044 (0.62); 2.6754 (0.57); 2.6707(0.75); 2.6665 (0.57); 2.5061 (82.21); 2.5017 (106.35); 2.4974 (80.71);2.3331 (0.68); 2.3285 (0.80); 2.3241 (0.62); 2.1873 (16.00); 2.1616(0.34); 2.1234 (0.87); 2.0923 (1.72); 2.0629 (0.98); 1.9890 (6.69);1.8252 (0.35); 1.8156 (0.36); 1.7896 (0.95); 1.7628 (0.71); 1.7556(0.67); 1.7450 (0.44); 1.5902 (0.34); 1.5619 (0.70); 1.5334 (0.66);1.1924 (1.85); 1.1746 (3.58); 1.1567 (1.78); 1.0251 (0.36); 1.0100(0.71); 0.9934 (0.97); 0.9767 (0.83); 0.9598 (0.43); 0.3804 (0.36);0.3721 (0.52); 0.3545 (0.94); 0.3450 (1.17); 0.3397 (0.98); 0.3306(0.59); 0.3261 (0.66); 0.3208 (0.53); 0.2060 (0.47); 0.1965 (0.59);0.1787 (2.77); 0.1712 (2.46); 0.1613 (4.41); 0.1471 (1.81); 0.1306(0.69); 0.1239 (0.52); −0.0002 (18.65);

Ex. 29, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0135 (7.84); 7.3476 (0.67); 7.3434 (0.92); 7.3236 (4.06); 7.3047(3.74); 7.2072 (1.33); 7.1516 (2.20); 7.1317 (1.88); 7.0725 (2.95);7.0206 (1.25); 7.0019 (2.21); 6.9833 (1.03); 6.9380 (1.52); 6.3834(3.20); 5.8869 (1.10); 5.8691 (1.27); 5.8593 (1.24); 5.8414 (1.13);5.7569 (7.59); 5.2407 (0.62); 5.1983 (2.49); 5.1598 (2.44); 5.1435(0.40); 5.1174 (0.61); 4.8819 (6.04); 4.8760 (5.98); 4.3626 (0.64);4.3296 (0.68); 4.0378 (0.65); 4.0200 (0.68); 4.0021 (0.48); 3.9904(0.61); 3.9553 (0.67); 3.8993 (1.18); 3.8714 (1.36); 3.8563 (1.52);3.8286 (1.27); 3.5890 (1.60); 3.5831 (3.49); 3.5772 (1.54); 3.3906(3.30); 3.3733 (1.28); 3.3630 (1.26); 3.3537 (0.71); 3.3437 (0.44);3.3342 (0.58); 3.2694 (1.85); 3.2515 (1.58); 3.2327 (0.95); 3.2266(1.72); 3.2086 (1.62); 2.8326 (0.45); 2.8049 (0.82); 2.7747 (0.46);2.5235 (0.47); 2.5103 (10.63); 2.5059 (21.60); 2.5013 (28.45); 2.4968(20.20); 2.4923 (9.50); 2.1611 (16.00); 2.1079 (0.61); 2.0790 (1.27);2.0498 (0.70); 1.9888 (2.84); 1.7766 (0.52); 1.7681 (0.55); 1.7455(0.52); 1.7377 (0.48); 1.5600 (0.52); 1.5504 (0.56); 1.5287 (0.52);1.5202 (0.50); 1.1922 (0.79); 1.1744 (1.56); 1.1566 (0.77); −0.0002(2.27);

Ex. 30, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0106 (9.66); 7.3122 (1.38); 7.3070 (1.86); 7.3034 (1.80); 7.2943(2.51); 7.2886 (2.37); 7.2843 (2.01); 7.2764 (1.66); 7.2723 (0.83);7.0618 (2.49); 7.0508 (0.46); 7.0417 (1.89); 6.9745 (1.36); 6.9548(2.36); 6.9377 (1.12); 6.4962 (4.47); 6.0804 (0.43); 6.0677 (0.97);6.0547 (0.71); 6.0413 (1.09); 6.0370 (0.58); 6.0288 (0.60); 6.0245(1.18); 6.0115 (0.82); 5.9980 (1.18); 5.9855 (0.55); 5.9178 (1.18);5.8999 (1.37); 5.8903 (1.39); 5.8721 (1.23); 5.7554 (3.77); 5.4426(0.62); 5.4384 (1.88); 5.4341 (1.98); 5.4300 (0.73); 5.3993 (0.58);5.3952 (1.62); 5.3909 (1.68); 5.3871 (0.62); 5.3490 (0.87); 5.3064(2.59); 5.2534 (2.66); 5.2461 (2.16); 5.2420 (2.00); 5.2195 (1.83);5.2153 (2.05); 5.2117 (1.56); 4.6321 (2.51); 4.6276 (2.73); 4.6198(2.65); 4.6153 (2.44); 4.3814 (0.71); 4.3488 (0.71); 4.0557 (0.89);4.0380 (2.66); 4.0202 (2.74); 4.0024 (1.04); 3.9835 (0.69); 3.9517(0.73); 3.8909 (1.34); 3.8629 (1.47); 3.8482 (1.72); 3.8203 (1.43);3.3995 (0.56); 3.3894 (0.39); 3.3797 (0.67); 3.3702 (1.17); 3.3609(0.78); 3.3268 (115.28); 3.3247 (244.25); 3.3015 (0.91); 3.2864 (2.05);3.2682 (2.05); 3.2607 (1.05); 3.2435 (1.55); 3.2256 (1.84); 2.8595(0.57); 2.8298 (0.90); 2.7999 (0.55); 2.6748 (0.44); 2.6703 (0.54);2.6664 (0.41); 2.5237 (0.95); 2.5058 (64.08); 2.5015 (86.96); 2.4974(61.07); 2.3329 (0.35); 2.3282 (0.54); 2.2059 (16.00); 2.1941 (0.82);2.1281 (0.63); 2.0918 (1.32); 2.0736 (0.76); 2.0642 (0.77); 1.9885(11.91); 1.8144 (0.55); 1.8073 (0.61); 1.7843 (0.55); 1.7789 (0.51);1.5723 (0.55); 1.5625 (0.61); 1.5404 (0.55); 1.5319 (0.53); 1.2345(0.56); 1.1924 (3.16); 1.1746 (6.25); 1.1568 (3.04); 0.0079 (0.33);−0.0002 (11.83); −0.0085 (0.37);

Ex. 31, Solvent: DMSO, Spectrometer: 399.95 MHz

8.3169 (0.34); 7.9747 (8.93); 7.9522 (0.97); 7.4350 (0.80); 7.4180(1.07); 7.4139 (1.72); 7.3971 (1.75); 7.3930 (1.11); 7.3762 (0.89);7.0110 (2.57); 7.0008 (1.74); 6.9899 (2.33); 6.9122 (1.26); 6.8907(1.42); 6.8870 (1.50); 6.8637 (4.65); 6.7266 (1.72); 6.2950 (3.82);6.0724 (1.10); 6.0500 (1.32); 6.0419 (1.26); 6.0194 (1.13); 5.2657(0.82); 5.2232 (2.61); 5.1774 (2.57); 5.1348 (0.81); 4.8525 (3.55);4.8470 (6.21); 4.8414 (3.66); 4.3937 (0.74); 4.3602 (0.80); 4.0551(0.76); 4.0373 (2.39); 4.0195 (2.94); 4.0018 (1.14); 3.9812 (0.77);3.8099 (0.72); 3.7790 (0.84); 3.7698 (0.99); 3.7669 (1.02); 3.7372(0.91); 3.5476 (1.82); 3.5417 (4.04); 3.5358 (1.85); 3.5253 (1.31);3.5026 (1.25); 3.4824 (0.95); 3.4600 (0.95); 3.4161 (0.53); 3.4070(0.38); 3.3965 (0.62); 3.3873 (1.11); 3.3783 (0.68); 3.3685 (0.47);3.3585 (0.75); 3.3498 (0.69); 3.3283 (104.73); 3.2962 (0.61); 3.2647(0.99); 3.2365 (0.56); 2.8903 (8.29); 2.8628 (0.53); 2.8318 (0.94);2.8049 (0.53); 2.7307 (6.62); 2.6753 (0.50); 2.6709 (0.72); 2.6662(0.52); 2.5406 (0.38); 2.5384 (0.40); 2.5241 (2.78); 2.5193 (4.33);2.5107 (39.51); 2.5063 (79.45); 2.5018 (104.79); 2.4972 (76.32); 2.4928(37.44); 2.3332 (0.55); 2.3286 (0.74); 2.3241 (0.57); 2.1883 (16.00);2.1484 (0.75); 2.1130 (1.45); 2.0836 (0.83); 1.9888 (10.32); 1.8011(0.62); 1.7797 (0.58); 1.5861 (0.59); 1.5773 (0.65); 1.5554 (0.62);1.5467 (0.60); 1.3974 (2.06); 1.1925 (2.75); 1.1747 (5.55); 1.1569(2.69); 0.0079 (0.70); −0.0002 (20.09); −0.0085 (0.85);

Ex. 32, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0176 (3.53); 7.6012 (1.82); 7.3438 (0.44); 7.3239 (1.89); 7.3050(1.73); 7.1513 (1.01); 7.1313 (0.86); 7.0203 (0.58); 7.0018 (1.01);6.9830 (0.46); 5.8875 (0.50); 5.8696 (0.59); 5.8598 (0.57); 5.8420(0.53); 5.6352 (0.42); 5.5923 (0.93); 5.5228 (0.92); 5.4798 (0.41);4.8815 (2.80); 4.8756 (2.78); 4.3512 (0.34); 4.3165 (0.35); 3.9344(0.35); 3.9003 (0.52); 3.8724 (0.60); 3.8573 (0.67); 3.8295 (0.57);3.5881 (0.71); 3.5822 (1.50); 3.5764 (0.68); 3.3790 (0.49); 3.3500(0.35); 3.3277 (40.02); 3.2700 (1.02); 3.2523 (0.72); 3.2272 (0.67);3.2094 (0.60); 2.8910 (2.35); 2.8506 (0.43); 2.7317 (1.82); 2.6713(0.43); 2.5246 (1.46); 2.5198 (2.36); 2.5112 (24.23); 2.5068 (48.55);2.5023 (63.46); 2.4977 (45.99); 2.4933 (22.44); 2.3289 (0.43); 2.0945(0.63); 2.0639 (0.35); 1.3977 (16.00); −0.0002 (1.78);

Ex. 33, Solvent: DMSO, Spectrometer: 399.95 MHz

8.3173 (0.68); 8.0139 (16.00); 7.6009 (9.09); 7.3088 (4.66); 7.3047(4.26); 7.2943 (5.83); 7.2901 (6.33); 7.2765 (3.38); 7.0614 (5.55);7.0397 (4.29); 6.9733 (3.12); 6.9546 (5.42); 6.9358 (2.50); 6.0796(0.81); 6.0671 (1.68); 6.0536 (1.40); 6.0405 (1.96); 6.0366 (1.26);6.0280 (1.17); 6.0238 (2.13); 6.0105 (1.61); 5.9973 (2.06); 5.9849(1.00); 5.9180 (2.65); 5.9001 (3.04); 5.8902 (3.03); 5.8722 (2.72);5.6336 (2.15); 5.5908 (4.85); 5.5228 (4.85); 5.4798 (2.17); 5.4387(3.78); 5.4344 (3.96); 5.4155 (0.38); 5.3954 (3.29); 5.3911 (3.43);5.3759 (0.33); 5.2445 (3.75); 5.2407 (3.86); 5.2180 (3.49); 5.2142(3.58); 4.6664 (0.38); 4.6541 (0.44); 4.6318 (5.77); 4.6274 (6.54);4.6202 (6.39); 4.6156 (5.84); 4.5935 (0.50); 4.5812 (0.41); 4.3499(1.84); 4.3167 (1.94); 3.9705 (1.72); 3.9352 (1.91); 3.8923 (2.66);3.8643 (2.99); 3.8494 (3.43); 3.8215 (2.94); 3.4082 (1.20); 3.3989(0.91); 3.3887 (1.47); 3.3795 (2.48); 3.3704 (1.57); 3.3599 (1.12);3.3504 (1.69); 3.3269 (87.89); 3.3030 (7.09); 3.2871 (3.80); 3.2691(5.63); 3.2441 (3.72); 3.2264 (3.21); 2.8786 (1.28); 2.8514 (2.32);2.8211 (1.31); 2.6757 (0.86); 2.6713 (1.15); 2.6670 (0.87); 2.5414(0.76); 2.5066 (123.19); 2.5022 (163.13); 2.4979 (124.07); 2.3335(0.90); 2.3290 (1.20); 2.3248 (0.94); 2.1240 (1.68); 2.0916 (3.54);2.0619 (1.97); 1.9891 (0.84); 1.8341 (0.60); 1.8240 (0.72); 1.8030(1.46); 1.7945 (1.59); 1.7721 (1.44); 1.7641 (1.35); 1.7424 (0.61);1.7329 (0.47); 1.5797 (0.59); 1.5699 (0.72); 1.5492 (1.44); 1.5399(1.58); 1.5186 (1.47); 1.5092 (1.41); 1.4889 (0.62); 1.4785 (0.50);1.3976 (8.31); 1.3512 (0.60); 1.3361 (1.33); 1.2587 (0.34); 1.2495(0.99); 1.2251 (1.13); 1.1750 (0.46); 0.1460 (0.57); 0.0079 (5.94);−0.0002 (128.33); −0.0083 (6.23); −0.1496 (0.60);

Ex. 34, Solvent: CD3CN, Spectrometer: 399.95 MHz

7.7083 (6.06); 7.5436 (1.24); 7.5244 (2.00); 7.4725 (0.75); 7.4677(0.83); 7.4555 (1.21); 7.4509 (1.48); 7.4360 (0.76); 7.4314 (1.48);7.4274 (1.02); 7.4129 (2.75); 7.4081 (1.86); 7.4023 (2.05); 7.3989(1.79); 7.3852 (1.24); 7.3825 (1.31); 7.3662 (0.41); 7.3628 (0.37);6.3912 (3.38); 6.0855 (1.21); 6.0633 (1.45); 6.0581 (1.40); 6.0359(1.26); 5.4478 (5.74); 5.1282 (0.63); 5.0861 (3.18); 5.0549 (3.16);5.0129 (0.64); 4.5808 (1.36); 4.5455 (2.82); 4.4959 (0.73); 4.4847(3.37); 4.4639 (0.73); 4.4494 (1.65); 3.9738 (1.43); 3.9462 (2.02);3.9303 (1.85); 3.9137 (0.75); 3.9028 (1.91); 3.3696 (0.71); 3.3643(1.81); 3.3508 (0.73); 3.3420 (2.72); 3.3317 (0.72); 3.3208 (1.99);3.3123 (1.18); 3.2988 (1.58); 3.2815 (0.95); 3.2526 (0.53); 3.2460(0.49); 2.9728 (0.42); 2.9425 (16.00); 2.8825 (0.46); 2.8759 (0.51);2.8498 (0.86); 2.8452 (0.88); 2.8188 (0.51); 2.8123 (0.47); 2.2256(16.31); 2.1817 (12.52); 2.1786 (12.84); 2.1203 (0.72); 1.9638 (0.83);1.9575 (0.80); 1.9519 (5.16); 1.9457 (9.51); 1.9396 (13.00); 1.9333(8.89); 1.9272 (4.50); 1.8732 (0.60); 1.8635 (0.62); 1.8421 (0.57);1.8324 (0.55); 1.7053 (0.63); 1.6953 (0.64); 1.6740 (0.59); 1.6643(0.56); −0.0002 (3.21);

Ex. 35, Solvent: CD3CN, Spectrometer: 399.95 MHz

7.7009 (3.52); 7.6949 (4.85); 7.5121 (1.27); 7.5082 (1.60); 7.4918(2.04); 7.4223 (0.34); 7.4175 (0.72); 7.4104 (0.57); 7.4006 (1.27);7.3950 (1.13); 7.3861 (1.41); 7.3812 (1.44); 7.3763 (1.15); 7.3677(2.28); 7.3640 (2.54); 7.3617 (1.79); 7.3585 (2.13); 7.3522 (2.26);7.3487 (2.27); 7.3418 (1.45); 7.3377 (1.01); 7.3235 (0.47); 6.3904(4.15); 6.0731 (0.94); 6.0512 (1.11); 6.0456 (1.19); 6.0237 (1.08);6.0196 (0.87); 6.0142 (0.75); 5.9917 (0.66); 5.4467 (3.81); 5.1259(0.73); 5.0839 (3.90); 5.0530 (3.81); 5.0317 (0.67); 5.0109 (0.74);4.4964 (0.77); 4.4626 (0.80); 4.2284 (1.10); 4.1947 (1.44); 4.1428(0.66); 4.1094 (3.41); 4.0957 (3.50); 4.0623 (0.68); 3.9871 (1.62);3.9533 (1.80); 3.9362 (1.72); 3.9104 (1.93); 3.9087 (2.05); 3.8950(1.38); 3.8929 (1.62); 3.8654 (1.49); 3.3778 (0.36); 3.3664 (1.37);3.3556 (1.62); 3.3489 (0.89); 3.3437 (1.36); 3.3395 (1.57); 3.3337(1.73); 3.3228 (1.26); 3.3121 (2.35); 3.3008 (1.28); 3.2903 (1.64);3.2817 (1.12); 3.2527 (0.60); 3.2462 (0.56); 2.8823 (0.50); 2.8759(0.55); 2.8456 (0.98); 2.8188 (0.56); 2.8124 (0.52); 2.5676 (16.00);2.5203 (10.63); 2.2257 (18.95); 2.2113 (1.50); 2.2100 (1.47); 2.1508(8.92); 2.1450 (7.66); 2.1193 (0.89); 2.1068 (0.44); 1.9635 (1.26);1.9573 (1.46); 1.9516 (10.81); 1.9454 (20.09); 1.9392 (27.69); 1.9330(18.99); 1.9268 (9.78); 1.9026 (0.38); 1.8925 (0.39); 1.8717 (0.71);1.8624 (0.72); 1.8409 (0.66); 1.8313 (0.65); 1.7249 (0.36); 1.7047(0.71); 1.6945 (0.74); 1.6736 (0.67); 1.6638 (0.65); −0.0002 (6.43);

Ex. 36, Solvent: CD3CN, Spectrometer: 399.95 MHz

7.6978 (9.56); 7.6946 (9.81); 7.5034 (2.47); 7.4953 (1.98); 7.4871(3.22); 7.4786 (2.25); 7.4120 (1.37); 7.4058 (1.29); 7.4041 (1.31);7.3961 (2.49); 7.3894 (3.75); 7.3832 (1.79); 7.3780 (2.98); 7.3709(3.94); 7.3642 (5.25); 7.3592 (7.40); 7.3502 (4.68); 7.3463 (4.48);7.3432 (4.31); 7.3389 (3.50); 7.3255 (0.77); 7.3199 (0.36); 6.3904(9.09); 6.0559 (2.04); 6.0490 (1.54); 6.0337 (2.46); 6.0279 (3.38);6.0213 (1.74); 6.0064 (2.11); 5.9989 (1.53); 5.4461 (6.12); 5.1259(1.72); 5.0837 (8.68); 5.0527 (8.53); 5.0108 (1.70); 4.4966 (1.86);4.4630 (1.92); 4.1672 (2.48); 4.1336 (3.50); 4.0704 (16.00); 3.9820(3.65); 3.9483 (4.37); 3.9368 (3.21); 3.9335 (3.07); 3.9090 (4.03);3.9059 (3.83); 3.8938 (2.76); 3.8900 (2.90); 3.8659 (2.47); 3.8624(2.68); 3.3719 (4.90); 3.3580 (1.20); 3.3497 (5.82); 3.3392 (3.46);3.3289 (5.33); 3.3192 (2.12); 3.3068 (4.84); 3.2814 (2.60); 3.2524(1.42); 3.2458 (1.31); 2.8770 (1.70); 2.8581 (2.13); 2.8442 (3.34);2.8396 (3.03); 2.8252 (3.07); 2.8203 (2.47); 2.8172 (2.63); 2.8064(3.31); 2.8032 (2.20); 2.7871 (1.40); 2.7842 (1.81); 2.7653 (0.57);2.7494 (0.72); 2.7307 (2.29); 2.7121 (2.41); 2.6978 (1.98); 2.6937(0.98); 2.6795 (2.88); 2.6611 (2.11); 2.6468 (1.21); 2.6427 (0.66);2.6283 (1.11); 2.6097 (0.36); 2.2254 (41.56); 2.2087 (1.66); 2.2029(1.75); 2.1611 (2.89); 2.1390 (18.09); 2.1203 (2.04); 1.9630 (1.87);1.9511 (16.20); 1.9450 (29.63); 1.9388 (40.14); 1.9327 (27.43); 1.9265(14.03); 1.9023 (0.82); 1.8919 (0.82); 1.8718 (1.68); 1.8617 (1.74);1.8404 (1.58); 1.8309 (1.54); 1.8101 (0.64); 1.7999 (0.57); 1.7351(0.72); 1.7243 (0.80); 1.7045 (1.69); 1.6944 (1.75); 1.6737 (1.59);1.6637 (1.55); 1.6429 (0.64); 1.6325 (0.58); 1.3112 (7.82); 1.2978(7.09); 1.2924 (15.87); 1.2792 (12.26); 1.2737 (8.02); 1.2605 (5.50);0.0078 (0.36); −0.0002 (8.65); −0.0086 (0.33);

Ex. 37, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0640 (0.47); 7.9724 (5.06); 7.9511 (0.92); 7.3757 (0.61); 7.3547(1.09); 7.3396 (1.18); 7.3184 (0.67); 7.0292 (1.63); 7.0201 (0.65);7.0080 (1.47); 7.0004 (1.26); 6.8829 (1.40); 6.8633 (2.63); 6.8505(0.94); 6.8289 (0.81); 6.7465 (0.55); 6.7262 (1.23); 6.3413 (1.14);6.3002 (3.02); 5.3924 (0.49); 5.2614 (0.62); 5.2194 (1.88); 5.1719(1.92); 5.1299 (0.63); 5.1053 (3.31); 4.9229 (3.83); 4.9172 (3.95);4.3945 (0.59); 4.3594 (0.64); 4.2667 (0.94); 4.2556 (1.08); 4.2437(1.05); 4.0560 (0.58); 4.0383 (1.66); 4.0204 (2.05); 4.0029 (0.99);3.9777 (0.72); 3.7070 (1.48); 3.7025 (1.60); 3.6939 (2.25); 3.6801(3.32); 3.6706 (2.57); 3.6521 (5.30); 3.5928 (2.49); 3.5858 (2.97);3.3779 (5389.76); 2.8920 (7.63); 2.8662 (0.93); 2.8312 (1.23); 2.8031(0.88); 2.7325 (6.18); 2.6785 (3.59); 2.6739 (4.83); 2.6694 (3.59);2.5409 (3.16); 2.5272 (16.53); 2.5224 (24.16); 2.5137 (251.32); 2.5094(502.31); 2.5049 (656.43); 2.5003 (472.57); 2.4960 (230.06); 2.3692(1.31); 2.3360 (3.51); 2.3315 (4.73); 2.3269 (3.82); 2.2414 (5.87);2.2071 (0.91); 2.1905 (12.67); 2.1730 (1.01); 2.1055 (1.36); 2.0721(16.00); 1.9889 (6.86); 1.9101 (1.98); 1.7874 (0.66); 1.7687 (0.63);1.6120 (1.12); 1.5918 (6.80); 1.5472 (0.60); 1.4104 (0.83); 1.2356(0.72); 1.1928 (1.94); 1.1750 (3.75); 1.1572 (1.90); −0.0002 (2.02);

Ex. 38, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0193 (3.81); 7.9536 (9.31); 7.9287 (0.71); 7.4111 (1.90); 7.3903(3.70); 7.3699 (2.77); 7.1618 (3.41); 7.1554 (4.01); 7.1404 (2.83);7.1355 (3.52); 7.0500 (2.52); 7.0308 (3.07); 6.9990 (3.46); 6.8590(1.95); 6.8395 (1.66); 6.2332 (1.49); 6.2085 (1.94); 6.2024 (1.88);6.1777 (1.58); 5.7531 (5.37); 4.8383 (0.39); 4.8325 (0.42); 4.7981(3.37); 4.7912 (5.19); 4.7841 (3.81); 4.7499 (0.40); 4.7439 (0.43);4.1809 (1.91); 4.1469 (2.02); 4.0379 (0.72); 4.0201 (0.75); 3.7672(1.17); 3.7363 (1.43); 3.7251 (2.07); 3.6943 (1.70); 3.5841 (1.95);3.5593 (1.99); 3.5420 (1.43); 3.5173 (1.40); 3.5040 (0.41); 3.4453(2.54); 3.4396 (4.79); 3.4338 (2.75); 3.3583 (517.73); 3.3548 (636.88);3.3514 (650.80); 3.3476 (856.85); 3.1850 (0.58); 3.1755 (0.57); 3.1584(0.59); 3.1523 (0.69); 3.0153 (1.49); 2.9857 (2.67); 2.9568 (1.50);2.9081 (0.89); 2.6766 (1.32); 2.6721 (1.80); 2.6676 (1.36); 2.5393(1.01); 2.5254 (5.57); 2.5206 (8.48); 2.5119 (93.76); 2.5075 (189.89);2.5030 (252.19); 2.4984 (187.91); 2.4941 (94.93); 2.3343 (1.28); 2.3297(1.75); 2.3252 (1.31); 2.2726 (0.33); 2.2336 (15.38); 2.1124 (16.00);2.0727 (3.08); 1.9886 (3.35); 1.7027 (0.68); 1.6747 (1.49); 1.6473(1.35); 1.6187 (0.51); 1.2360 (0.51); 1.1925 (0.89); 1.1747 (1.77);1.1569 (0.86); −0.0002 (4.40);

Ex. 39, Solvent: DMSO, Spectrometer: 399.95 MHz

8.1588 (3.15); 7.9410 (9.29); 7.3715 (1.93); 7.3509 (4.10); 7.3300(4.13); 7.3227 (3.11); 7.2026 (2.15); 7.1817 (3.00); 7.1038 (2.36);7.1016 (3.27); 7.0883 (2.72); 7.0832 (6.50); 7.0681 (1.94); 7.0626(3.65); 6.2591 (1.36); 6.2356 (1.73); 6.2282 (1.60); 6.2046 (1.40);5.8317 (0.37); 5.8181 (0.77); 5.8051 (0.72); 5.7917 (0.90); 5.7888(0.58); 5.7782 (0.52); 5.7748 (0.98); 5.7617 (0.88); 5.7533 (7.80);5.7488 (1.23); 5.7350 (0.48); 5.2725 (0.61); 5.2686 (1.79); 5.2645(1.88); 5.2607 (0.73); 5.2291 (0.52); 5.2253 (1.53); 5.2212 (1.58);5.2173 (0.60); 5.0153 (1.67); 5.0116 (1.68); 4.9889 (1.55); 4.9852(1.59); 4.5819 (0.45); 4.5687 (0.48); 4.5502 (1.39); 4.5369 (1.39);4.5231 (1.42); 4.5090 (1.36); 4.4913 (0.49); 4.4809 (0.36); 4.4771(0.45); 4.1741 (1.49); 4.1408 (1.58); 4.0559 (0.39); 4.0381 (1.22);4.0202 (1.23); 4.0025 (0.42); 3.7617 (1.06); 3.7306 (1.30); 3.7197(1.87); 3.6887 (1.52); 3.5785 (1.71); 3.5549 (1.74); 3.5365 (1.20);3.5130 (1.25); 3.3616 (206.47); 3.3582 (217.30); 3.3552 (181.25); 3.3479(336.94); 3.0516 (1.16); 3.0221 (2.01); 2.9935 (1.15); 2.9264 (0.94);2.6768 (0.56); 2.6722 (0.78); 2.6677 (0.55); 2.5257 (2.16); 2.5210(3.11); 2.5123 (41.85); 2.5078 (87.47); 2.5032 (117.61); 2.4986 (86.11);2.4940 (42.20); 2.3344 (0.60); 2.3299 (0.82); 2.3253 (0.61); 2.1553(16.00); 2.1044 (1.29); 2.0730 (1.96); 1.9887 (5.62); 1.7272 (0.42);1.7174 (0.54); 1.6955 (1.13); 1.6874 (1.27); 1.6656 (1.19); 1.6575(1.10); 1.6361 (0.48); 1.6262 (0.40); 1.2350 (0.36); 1.1926 (1.55);1.1748 (3.07); 1.1570 (1.50); −0.0002 (2.02);

Ex. 40, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0340 (9.26); 7.4541 (1.53); 7.4344 (3.45); 7.4147 (2.25); 7.2915(1.97); 7.2722 (1.59); 7.1628 (1.73); 7.1577 (2.93); 7.1533 (2.10);7.1184 (1.43); 7.1162 (1.62); 7.1127 (1.30); 7.1104 (1.26); 7.0983(1.34); 7.0961 (1.38); 7.0927 (1.25); 7.0903 (1.15); 6.4980 (4.43);5.7802 (1.13); 5.7604 (1.37); 5.7531 (1.33); 5.7332 (1.17); 5.3497(0.88); 5.3073 (2.72); 5.2577 (2.67); 5.2151 (0.88); 5.1965 (0.85);4.3847 (0.72); 4.3507 (0.77); 4.0557 (0.72); 4.0379 (2.19); 4.0201(2.25); 4.0023 (0.93); 3.9883 (0.68); 3.9532 (0.75); 3.9232 (1.23);3.8957 (1.41); 3.8800 (1.64); 3.8527 (1.33); 3.4089 (1.99); 3.3998(0.57); 3.3890 (2.04); 3.3807 (1.25); 3.3707 (0.96); 3.3655 (1.83);3.3456 (3.26); 3.3292 (241.15); 3.3261 (302.53); 3.2659 (1.26); 3.2371(0.70); 3.0429 (1.96); 2.8659 (0.52); 2.8546 (1.70); 2.8352 (0.92);2.8076 (0.53); 2.6753 (0.51); 2.6707 (0.71); 2.6662 (0.53); 2.5409(0.35); 2.5241 (1.21); 2.5192 (1.89); 2.5106 (36.46); 2.5061 (78.71);2.5015 (111.02); 2.4969 (83.92); 2.4925 (41.55); 2.3329 (0.55); 2.3283(0.77); 2.3238 (0.58); 2.2070 (16.00); 2.1924 (1.81); 2.1325 (0.67);2.1004 (1.39); 2.0735 (1.03); 1.9885 (9.76); 1.9183 (0.43); 1.9063(0.85); 1.8989 (0.95); 1.8956 (0.73); 1.8870 (1.65); 1.8813 (0.75);1.8750 (0.97); 1.8676 (1.00); 1.8557 (0.74); 1.8447 (0.33); 1.8248(0.61); 1.8157 (0.64); 1.7930 (0.58); 1.7849 (0.55); 1.5824 (0.56);1.5734 (0.62); 1.5523 (0.58); 1.5439 (0.58); 1.3976 (0.58); 1.2355(0.40); 1.1923 (2.67); 1.1745 (5.40); 1.1567 (2.63); 1.0807 (0.55);1.0670 (1.78); 1.0595 (3.41); 1.0558 (1.68); 1.0530 (1.79); 1.0470(1.69); 1.0392 (3.51); 1.0334 (2.18); 1.0311 (2.14); 1.0249 (3.40);1.0179 (3.09); 1.0139 (3.90); 1.0060 (1.80); 0.9919 (0.44); 0.0080(1.09); −0.0002 (35.44); −0.0085 (1.38);

Ex. 41, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0259 (9.47); 7.3231 (1.61); 7.3190 (0.50); 7.3027 (3.67); 7.2952(0.37); 7.2825 (2.20); 6.9632 (4.18); 6.9580 (3.28); 6.9534 (2.20);6.9445 (1.95); 6.9304 (1.59); 6.9278 (1.49); 6.9245 (1.19); 6.9221(1.11); 6.9097 (1.41); 6.9079 (1.39); 6.9036 (1.22); 6.4980 (4.40);6.0822 (0.43); 6.0692 (0.96); 6.0560 (0.94); 6.0428 (1.11); 6.0390(0.59); 6.0298 (0.60); 6.0259 (1.19); 6.0128 (1.05); 5.9996 (1.20);5.9866 (0.57); 5.7179 (1.17); 5.6978 (1.40); 5.6911 (1.37); 5.6706(1.21); 5.4168 (0.67); 5.4126 (1.94); 5.4082 (2.03); 5.4039 (0.75);5.3737 (0.62); 5.3694 (1.73); 5.3650 (1.80); 5.3607 (0.77); 5.3504(0.89); 5.3076 (2.74); 5.2632 (2.49); 5.2590 (4.21); 5.2407 (0.78);5.2370 (1.73); 5.2328 (1.74); 5.2294 (0.81); 5.2153 (0.92); 5.1968(0.86); 4.5810 (2.25); 4.5772 (4.03); 4.5735 (2.51); 4.5680 (2.46);4.5642 (4.01); 4.5606 (2.36); 4.3853 (0.73); 4.3525 (0.77); 4.0377(0.73); 4.0200 (0.78); 4.0021 (0.45); 3.9890 (0.69); 3.9532 (0.73);3.8941 (1.27); 3.8670 (1.46); 3.8512 (1.69); 3.8239 (1.42); 3.4095(0.54); 3.3929 (1.96); 3.3809 (1.27); 3.3725 (2.16); 3.3619 (0.42);3.3500 (2.09); 3.3262 (194.10); 3.3243 (226.61); 3.3220 (303.73); 3.2983(3.23); 3.2653 (1.26); 3.2367 (0.64); 3.2314 (0.57); 3.0428 (2.05);2.8659 (0.53); 2.8544 (1.75); 2.8381 (0.92); 2.8086 (0.52); 2.6792(0.39); 2.6748 (0.88); 2.6702 (1.21); 2.6657 (0.89); 2.6612 (0.41);2.5406 (0.42); 2.5237 (2.26); 2.5188 (3.67); 2.5102 (61.32); 2.5057(131.73); 2.5011 (185.44); 2.4966 (139.12); 2.4921 (67.67); 2.3326(0.93); 2.3280 (1.24); 2.3234 (0.94); 2.3188 (0.50); 2.2068 (16.00);2.1923 (1.83); 2.1313 (0.66); 2.1023 (1.37); 2.0736 (1.16); 1.9884(3.47); 1.8230 (0.57); 1.8150 (0.63); 1.7916 (0.57); 1.7835 (0.54);1.5831 (0.57); 1.5736 (0.63); 1.5521 (0.59); 1.5421 (0.57); 1.3976(0.32); 1.2583 (0.39); 1.2493 (0.59); 1.2354 (0.71); 1.1922 (0.94);1.1744 (1.90); 1.1566 (0.93); 0.0080 (2.08); −0.0002 (68.81); −0.0085(2.53);

Ex. 42, Solvent: DMSO, Spectrometer: 601.6 MHz

8.0198 (3.29); 7.9396 (10.59); 7.3640 (2.27); 7.3503 (4.58); 7.3366(2.94); 7.1002 (2.64); 7.0987 (3.30); 7.0868 (2.70); 7.0852 (2.96);7.0813 (2.45); 7.0671 (2.24); 7.0451 (2.24); 7.0324 (2.55); 6.9980(2.70); 6.8566 (1.49); 6.8547 (1.50); 6.8439 (1.31); 6.8421 (1.31);6.2494 (1.52); 6.2337 (1.82); 6.2287 (1.73); 6.2131 (1.56); 5.8156(0.47); 5.8065 (0.92); 5.7978 (0.85); 5.7890 (1.03); 5.7869 (0.64);5.7799 (0.59); 5.7777 (1.10); 5.7690 (0.94); 5.7602 (1.06); 5.7555(1.13); 5.7512 (0.57); 5.2645 (0.67); 5.2618 (2.03); 5.2591 (2.05);5.2564 (0.74); 5.2357 (0.62); 5.2331 (1.79); 5.2303 (1.85); 5.2277(0.64); 5.0126 (0.70); 5.0104 (1.86); 5.0079 (1.83); 5.0057 (0.74);4.9951 (0.68); 4.9929 (1.76); 4.9904 (1.76); 4.9882 (0.71); 4.5755(0.35); 4.5732 (0.62); 4.5708 (0.38); 4.5667 (0.38); 4.5644 (0.63);4.5621 (0.37); 4.5544 (0.78); 4.5521 (1.36); 4.5497 (0.85); 4.5456(0.80); 4.5433 (1.33); 4.5410 (0.78); 4.5214 (0.78); 4.5192 (1.35);4.5170 (0.83); 4.5120 (0.80); 4.5098 (1.34); 4.5077 (0.79); 4.5004(0.38); 4.4981 (0.66); 4.4958 (0.40); 4.4910 (0.37); 4.4887 (0.63);4.4865 (0.37); 4.1690 (1.42); 4.1468 (1.48); 4.0466 (1.14); 4.0348(3.48); 4.0229 (3.47); 4.0111 (1.16); 3.7493 (1.28); 3.7286 (1.61);3.7214 (1.98); 3.7008 (1.62); 3.5691 (1.84); 3.5535 (1.86); 3.5413(1.45); 3.5257 (1.45); 3.3579 (0.37); 3.3517 (0.85); 3.3481 (0.61);3.3454 (0.84); 3.3251 (591.42); 3.3079 (1.11); 3.3012 (4.55); 3.0160(0.87); 3.0123 (1.06); 2.9927 (1.95); 2.9738 (1.08); 2.9701 (0.92);2.6190 (0.40); 2.6160 (0.88); 2.6130 (1.25); 2.6099 (0.90); 2.6069(0.41); 2.5405 (0.37); 2.5223 (3.07); 2.5192 (3.82); 2.5161 (3.46);2.5074 (64.00); 2.5043 (141.18); 2.5012 (196.75); 2.4981 (141.80);2.4951 (65.39); 2.3915 (0.37); 2.3885 (0.85); 2.3854 (1.21); 2.3823(0.86); 2.3793 (0.38); 2.2327 (12.96); 2.1103 (13.21); 2.0890 (1.16);2.0837 (1.23); 2.0734 (1.26); 2.0670 (1.33); 1.9884 (16.00); 1.6966(0.39); 1.6905 (0.47); 1.6763 (1.08); 1.6704 (1.18); 1.6561 (1.12);1.6504 (1.09); 1.6365 (0.44); 1.6299 (0.37); 1.3976 (0.40); 1.1862(4.45); 1.1744 (9.23); 1.1626 (4.25); 0.0053 (0.64); −0.0002 (24.12);−0.0057 (0.68);

Ex. 43, Solvent: CD3CN, Spectrometer: 399.95 MHz

7.7017 (16.00); 7.5291 (2.62); 7.5095 (4.66); 7.4599 (1.87); 7.4556(2.02); 7.4419 (3.09); 7.4379 (4.17); 7.4302 (2.69); 7.4189 (4.14);7.4148 (6.16); 7.3934 (4.06); 7.3899 (3.96); 7.3753 (3.19); 7.3569(1.29); 7.3536 (1.16); 6.4212 (7.95); 6.0279 (2.81); 6.0066 (3.23);6.0002 (3.19); 5.9789 (2.93); 5.1548 (1.55); 5.1129 (7.73); 5.0841(7.77); 5.0630 (0.76); 5.0419 (1.47); 4.8696 (4.32); 4.8408 (6.69);4.7412 (7.05); 4.7123 (4.54); 4.5215 (1.52); 4.4876 (1.67); 4.1147(1.76); 4.0968 (5.36); 4.0790 (5.57); 4.0678 (1.89); 4.0612 (2.11);4.0560 (2.15); 4.0534 (1.43); 4.0451 (5.27); 4.0334 (5.47); 4.0225(5.45); 4.0107 (5.47); 4.0023 (1.59); 3.9998 (2.14); 3.9880 (2.51);3.9798 (2.25); 3.9570 (0.81); 3.9327 (4.54); 3.9049 (3.73); 3.8896(4.22); 3.8619 (4.00); 3.4070 (0.67); 3.3974 (1.35); 3.3878 (0.87);3.3783 (1.53); 3.3687 (2.87); 3.3591 (1.67); 3.3494 (2.09); 3.3407(2.44); 3.3303 (1.21); 3.3227 (4.99); 3.3136 (2.36); 3.3017 (4.58);3.2797 (4.61); 3.2586 (3.78); 2.9157 (1.05); 2.9093 (1.15); 2.8782(2.03); 2.8520 (1.17); 2.8454 (1.08); 2.4976 (0.34); 2.2545 (40.20);2.2208 (828.11); 2.2177 (745.43); 2.1497 (2.66); 2.1436 (2.69); 2.1374(2.27); 2.1312 (1.52); 2.1250 (0.99); 2.0912 (0.59); 2.0015 (24.43);1.9943 (7.48); 1.9880 (7.97); 1.9823 (68.62); 1.9762 (130.30); 1.9700(182.81); 1.9638 (126.48); 1.9576 (65.15); 1.9303 (1.19); 1.9197 (1.10);1.8997 (1.68); 1.8900 (1.75); 1.8680 (1.55); 1.8584 (1.52); 1.8382(0.87); 1.8278 (0.69); 1.8108 (0.60); 1.8046 (0.94); 1.7984 (1.25);1.7922 (0.94); 1.7861 (0.56); 1.7660 (0.75); 1.7553 (0.82); 1.7355(1.55); 1.7253 (1.60); 1.7042 (1.49); 1.6942 (1.45); 1.6744 (0.70);1.6635 (0.66); 1.4653 (1.05); 1.3891 (0.33); 1.2986 (1.87); 1.2504(6.62); 1.2326 (12.99); 1.2147 (6.49);

Ex. 44, Solvent: CD3CN, Spectrometer: 399.95 MHz

7.6732 (4.41); 7.4745 (0.94); 7.4565 (1.13); 7.4523 (1.04); 7.3852(0.53); 7.3812 (0.64); 7.3687 (1.08); 7.3640 (1.38); 7.3565 (1.61);7.3526 (1.54); 7.3477 (1.18); 7.3262 (1.14); 7.3226 (1.11); 7.3066(0.84); 6.3930 (2.25); 6.0032 (0.78); 5.9814 (0.93); 5.9756 (0.90);5.9538 (0.80); 5.1262 (0.46); 5.0841 (2.18); 5.0558 (2.16); 5.0139(0.41); 4.6676 (1.34); 4.6387 (2.06); 4.5397 (2.16); 4.5108 (1.47);4.4929 (0.48); 4.4592 (0.51); 4.0683 (0.55); 4.0504 (0.54); 3.9493(1.39); 3.9217 (1.31); 3.9062 (1.51); 3.8785 (1.11); 3.6257 (0.85);3.6130 (1.73); 3.6025 (3.17); 3.5924 (1.34); 3.5316 (2.71); 3.5217(2.79); 3.5177 (1.62); 3.5106 (1.21); 3.5076 (1.14); 3.3701 (0.38);3.3510 (0.45); 3.3413 (0.82); 3.3317 (0.51); 3.3194 (0.56); 3.3126(0.88); 3.2965 (16.00); 3.2833 (1.32); 3.2790 (1.78); 3.2675 (0.34);3.2573 (1.34); 3.2482 (0.40); 3.2357 (1.04); 3.2141 (1.01); 2.8782(0.34); 2.8476 (0.60); 2.8214 (0.34); 2.8155 (0.32); 2.4691 (0.44);2.2258 (12.47); 2.2245 (12.61); 2.2048 (274.24); 2.1995 (217.79); 2.1214(0.81); 2.1153 (0.79); 2.1091 (0.70); 2.1029 (0.44); 1.9729 (2.73);1.9659 (2.55); 1.9540 (26.83); 1.9478 (51.05); 1.9417 (70.86); 1.9355(49.44); 1.9293 (25.39); 1.9048 (0.46); 1.8942 (0.37); 1.8736 (0.51);1.8642 (0.53); 1.8424 (0.46); 1.8331 (0.47); 1.7763 (0.36); 1.7701(0.48); 1.7639 (0.36); 1.7087 (0.45); 1.6988 (0.48); 1.6775 (0.44);1.6675 (0.44); 1.2699 (0.61); 1.2218 (0.68); 1.2040 (1.33); 1.1862(0.67); −0.0002 (0.39);

Ex. 45, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0061 (9.48); 7.9826 (0.77); 7.6598 (0.38); 7.3440 (1.15); 7.3246(5.02); 7.3058 (4.59); 7.1517 (2.63); 7.1318 (2.19); 7.0473 (2.59);7.0283 (2.99); 7.0207 (2.26); 7.0000 (4.37); 6.9832 (1.47); 6.8561(1.85); 6.8393 (1.79); 5.8864 (1.24); 5.8686 (1.50); 5.8588 (1.54);5.8407 (1.30); 5.7552 (11.14); 4.8813 (6.84); 4.8756 (7.31); 4.1688(1.86); 4.1351 (1.96); 4.0375 (0.44); 4.0198 (0.43); 3.9005 (1.28);3.8727 (1.45); 3.8576 (1.70); 3.8298 (1.38); 3.5843 (1.93); 3.5785(3.88); 3.5727 (1.85); 3.3549 (49.56); 3.3360 (230.21); 3.3284 (217.08);3.3256 (287.42); 3.2867 (2.54); 3.2724 (2.74); 3.2544 (2.19); 3.2403(0.76); 3.2293 (1.76); 3.2115 (1.70); 3.1978 (0.45); 3.1549 (0.35);3.1491 (0.47); 2.9978 (1.36); 2.9676 (2.48); 2.9391 (1.36); 2.9078(7.08); 2.6750 (0.71); 2.6706 (0.96); 2.6662 (0.71); 2.5408 (0.63);2.5060 (108.78); 2.5015 (142.02); 2.4971 (107.62); 2.3326 (0.81); 2.3282(1.05); 2.3239 (0.84); 2.2620 (0.49); 2.2319 (14.26); 2.1266 (0.83);2.1063 (16.00); 2.0734 (2.22); 2.0429 (2.16); 1.9884 (1.83); 1.6864(0.67); 1.6787 (0.78); 1.6565 (1.51); 1.6485 (1.61); 1.6261 (1.49);1.6187 (1.39); 1.5966 (0.58); 1.5873 (0.47); 1.2581 (0.37); 1.2346(1.05); 1.1923 (0.52); 1.1745 (0.99); 1.1567 (0.51); 0.0079 (1.58);−0.0002 (26.90); −0.0083 (1.28);

Ex. 46, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0114 (3.98); 8.0029 (11.23); 7.3168 (0.64); 7.3102 (2.52); 7.3057(2.06); 7.2948 (3.13); 7.2911 (3.67); 7.2869 (2.38); 7.2770 (1.89);7.2727 (1.12); 7.0621 (2.97); 7.0470 (3.07); 7.0424 (2.86); 7.0400(2.62); 7.0278 (3.25); 6.9937 (3.44); 6.9741 (1.81); 6.9554 (2.92);6.9385 (1.31); 6.9367 (1.32); 6.8563 (1.94); 6.8404 (1.62); 6.8372(1.60); 6.0807 (0.50); 6.0682 (1.08); 6.0546 (0.80); 6.0417 (1.23);6.0374 (0.69); 6.0293 (0.63); 6.0249 (1.34); 6.0114 (0.91); 5.9984(1.32); 5.9860 (0.64); 5.9166 (1.45); 5.8987 (1.67); 5.8889 (1.66);5.8708 (1.52); 5.4429 (0.74); 5.4386 (2.25); 5.4343 (2.36); 5.4300(0.91); 5.3996 (0.64); 5.3953 (1.95); 5.3910 (2.07); 5.3867 (0.80);5.2483 (0.83); 5.2445 (2.18); 5.2405 (2.21); 5.2369 (0.89); 5.2218(0.75); 5.2180 (2.01); 5.2140 (2.08); 5.2104 (0.84); 4.6375 (1.28);4.6331 (2.95); 4.6284 (3.27); 4.6249 (2.68); 4.6210 (3.20); 4.6161(3.05); 4.1680 (1.90); 4.1345 (1.99); 4.0556 (1.04); 4.0378 (3.12);4.0200 (3.15); 4.0022 (1.05); 3.8925 (1.59); 3.8645 (1.82); 3.8497(2.08); 3.8218 (1.73); 3.3907 (0.37); 3.3748 (0.51); 3.3267 (710.58);3.2892 (3.58); 3.2791 (1.56); 3.2711 (2.91); 3.2574 (0.53); 3.2464(2.07); 3.2284 (2.00); 3.0001 (1.35); 2.9703 (2.48); 2.9418 (1.39);2.6795 (0.44); 2.6752 (0.98); 2.6706 (1.42); 2.6660 (1.05); 2.6614(0.52); 2.5408 (0.73); 2.5240 (2.28); 2.5193 (3.48); 2.5105 (71.10);2.5060 (152.70); 2.5014 (209.79); 2.4969 (155.79); 2.4924 (77.49);2.3373 (0.50); 2.3328 (1.07); 2.3282 (1.49); 2.3237 (1.12); 2.3191(0.57); 2.2321 (15.82); 2.1056 (16.00); 2.0735 (3.20); 2.0413 (1.86);1.9885 (13.82); 1.6890 (0.55); 1.6799 (0.66); 1.6586 (1.41); 1.6501(1.59); 1.6278 (1.45); 1.6193 (1.40); 1.5978 (0.57); 1.5879 (0.48);1.3976 (1.15); 1.2978 (0.39); 1.2583 (0.59); 1.2348 (1.38); 1.1923(3.77); 1.1745 (7.51); 1.1567 (3.71); −0.0002 (6.96);

Ex. 47, Solvent: DMSO, Spectrometer: 399.95 MHz

8.7845 (0.35); 8.0356 (1.18); 8.0319 (7.37); 8.0173 (0.49); 7.5869(0.42); 7.4420 (0.59); 7.4347 (3.88); 7.4182 (1.40); 7.4133 (4.68);7.3994 (0.34); 7.3507 (0.44); 7.1707 (0.68); 7.1642 (5.09); 7.1593(1.82); 7.1477 (1.45); 7.1427 (4.51); 7.1361 (0.67); 6.4984 (4.27);5.7729 (1.07); 5.7530 (1.32); 5.7460 (1.23); 5.7256 (1.00); 5.3488(0.82); 5.3061 (2.51); 5.2560 (2.62); 5.2135 (0.86); 4.3851 (0.72);4.3514 (0.78); 4.0558 (0.62); 4.0380 (1.84); 4.0202 (1.89); 4.0024(0.80); 3.9879 (0.71); 3.9524 (0.75); 3.9109 (1.03); 3.8837 (1.26);3.8679 (1.39); 3.8406 (1.14); 3.4604 (0.37); 3.4400 (0.63); 3.4132(2.35); 3.3927 (3.49); 3.3525 (353.69); 3.3485 (459.15); 3.3461(516.01); 3.3421 (735.82); 3.2661 (2.04); 3.2380 (1.15); 3.2318 (1.10);3.1922 (0.43); 2.8668 (0.59); 2.8363 (0.98); 2.8095 (0.58); 2.6807(0.41); 2.6763 (0.84); 2.6717 (1.18); 2.6672 (0.88); 2.6628 (0.45);2.5419 (0.62); 2.5251 (2.21); 2.5204 (3.20); 2.5117 (56.02); 2.5072(119.61); 2.5027 (163.85); 2.4981 (121.68); 2.4936 (60.83); 2.3385(0.42); 2.3340 (0.83); 2.3294 (1.15); 2.3249 (0.87); 2.3202 (0.44);2.2069 (16.00); 2.1340 (0.75); 2.1017 (1.45); 2.0861 (1.25); 2.0729(1.73); 1.9886 (8.30); 1.9241 (0.45); 1.9123 (0.85); 1.9045 (0.99);1.9016 (0.74); 1.8929 (1.48); 1.8887 (0.92); 1.8812 (0.96); 1.8732(0.96); 1.8615 (0.56); 1.8252 (0.61); 1.8148 (0.66); 1.7924 (0.59);1.7839 (0.57); 1.7603 (0.33); 1.6043 (0.33); 1.5838 (0.59); 1.5743(0.65); 1.5525 (0.63); 1.5443 (0.61); 1.3976 (1.15); 1.2349 (0.77);1.1925 (2.26); 1.1747 (4.49); 1.1569 (2.23); 1.1158 (0.39); 1.0957(0.36); 1.0830 (0.77); 1.0704 (1.81); 1.0631 (3.57); 1.0553 (2.15);1.0505 (1.85); 1.0431 (2.83); 1.0368 (1.75); 1.0246 (1.74); 1.0175(3.08); 1.0106 (3.01); 1.0063 (3.12); 0.9984 (2.10); 0.9854 (0.50);0.0080 (0.33); −0.0002 (11.67); −0.0084 (0.46);

Ex. 48, Solvent: DMSO, Spectrometer: 399.95 MHz

8.0329 (7.22); 7.4658 (0.49); 7.4552 (8.31); 7.4454 (4.85); 7.4417(4.76); 7.4214 (0.51); 7.2027 (0.35); 7.1921 (2.05); 7.1817 (1.81);7.1789 (1.98); 7.1687 (1.79); 6.5052 (4.35); 6.1109 (1.31); 6.0867(1.67); 6.0798 (1.60); 6.0555 (1.36); 5.7630 (9.67); 5.3651 (0.98);5.3226 (2.46); 5.2634 (2.42); 5.2208 (0.98); 4.3907 (0.71); 4.3580(0.75); 4.0544 (0.35); 4.0367 (1.07); 4.0189 (1.11); 4.0010 (0.69);3.9922 (0.67); 3.9571 (0.72); 3.9209 (1.11); 3.8896 (1.34); 3.8776(1.54); 3.8464 (1.23); 3.4331 (1.62); 3.4211 (0.73); 3.4089 (1.99);3.4016 (1.17); 3.3900 (3.25); 3.3692 (105.50); 3.3662 (108.97); 3.3627(125.98); 3.3573 (125.25); 3.3535 (153.94); 3.3133 (0.59); 3.2996(0.80); 3.2691 (1.11); 3.2411 (0.58); 3.0424 (0.57); 2.8682 (0.53);2.8540 (0.58); 2.8380 (0.90); 2.8106 (0.52); 2.6772 (0.44); 2.6726(0.62); 2.6680 (0.44); 2.5261 (1.16); 2.5214 (1.66); 2.5126 (31.65);2.5081 (69.43); 2.5035 (94.42); 2.4989 (67.38); 2.4944 (31.70); 2.3347(0.46); 2.3303 (0.64); 2.3257 (0.48); 2.2067 (16.00); 2.1915 (0.73);2.1337 (0.69); 2.1264 (0.52); 2.1033 (1.36); 2.0774 (1.16); 1.9902(4.94); 1.8206 (0.56); 1.8121 (0.62); 1.7897 (0.56); 1.7816 (0.52);1.6306 (0.37); 1.6183 (0.69); 1.6112 (0.91); 1.6056 (0.71); 1.5993(1.52); 1.5876 (1.00); 1.5796 (1.26); 1.5678 (1.05); 1.5464 (0.60);1.5370 (0.58); 1.1920 (1.38); 1.1742 (2.75); 1.1564 (1.35); 0.9614(0.64); 0.9531 (0.62); 0.9425 (2.08); 0.9294 (1.10); 0.9219 (2.04);0.9102 (0.90); 0.9030 (0.72); 0.8210 (0.39); 0.8110 (0.77); 0.8005(0.70); 0.7932 (0.89); 0.7835 (0.72); 0.7686 (0.74); 0.7586 (0.60);0.7470 (0.93); 0.7375 (0.80); 0.7268 (0.86); 0.7176 (0.60); 0.0080(0.72); −0.0002 (27.69); −0.0085 (1.03);

Ex. 49, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9775 (7.21); 7.9529 (0.74); 7.3985 (0.59); 7.3812 (0.71); 7.3775(1.25); 7.3604 (1.27); 7.3567 (0.82); 7.3395 (0.66); 6.9326 (1.66);6.9116 (1.52); 6.8657 (0.89); 6.8415 (1.10); 6.8200 (0.86); 6.5035(3.21); 6.0604 (0.81); 6.0378 (1.02); 6.0299 (0.96); 6.0070 (0.85);5.3679 (0.77); 5.3253 (1.93); 5.2637 (1.85); 5.2211 (0.75); 4.3962(0.51); 4.3632 (0.54); 4.1114 (1.81); 4.1006 (2.89); 4.0887 (1.95);4.0548 (0.57); 4.0370 (1.71); 4.0192 (1.75); 4.0013 (0.96); 3.9626(0.51); 3.7633 (0.56); 3.7322 (0.67); 3.7208 (0.99); 3.6903 (0.88);3.5957 (1.03); 3.5730 (1.06); 3.5536 (0.67); 3.5309 (0.66); 3.4820(1.31); 3.4783 (1.25); 3.4727 (2.14); 3.4652 (2.14); 3.4542 (1.04);3.4264 (0.43); 3.4069 (0.40); 3.3973 (0.75); 3.3870 (0.38); 3.3688(0.48); 3.3607 (0.74); 3.3419 (218.73); 3.3183 (1.43); 3.3079 (0.72);3.3033 (0.71); 3.2721 (0.80); 3.2654 (0.64); 3.2445 (0.46); 3.0407(0.36); 3.0169 (16.00); 2.8906 (6.62); 2.8700 (0.39); 2.8386 (0.74);2.8125 (0.39); 2.7310 (5.14); 2.6763 (0.36); 2.6718 (0.52); 2.6673(0.37); 2.5252 (0.78); 2.5206 (1.20); 2.5118 (26.94); 2.5073 (58.44);2.5028 (78.90); 2.4982 (55.83); 2.4937 (26.07); 2.3342 (0.39); 2.3295(0.54); 2.3249 (0.40); 2.2087 (12.09); 2.1393 (0.48); 2.1331 (0.49);2.1257 (0.45); 2.1104 (0.99); 2.0768 (0.66); 1.9899 (7.95); 1.9076(0.84); 1.8267 (0.44); 1.8211 (0.47); 1.7982 (0.43); 1.7900 (0.40);1.5843 (0.41); 1.5753 (0.46); 1.5538 (0.44); 1.5450 (0.43); 1.1920(2.10); 1.1742 (4.23); 1.1564 (2.04); 0.0080 (0.40); −0.0002 (14.85);−0.0085 (0.51);

Ex. 50, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9530 (8.91); 7.3744 (1.93); 7.3538 (4.10); 7.3332 (2.69); 7.1062(2.47); 7.1041 (3.28); 7.0859 (4.76); 7.0839 (4.63); 7.0648 (2.13);6.5062 (4.45); 6.2598 (1.34); 6.2363 (1.75); 6.2289 (1.61); 6.2053(1.41); 5.8253 (0.33); 5.8117 (0.67); 5.7985 (0.66); 5.7852 (0.82);5.7684 (0.90); 5.7616 (0.80); 5.7552 (0.78); 5.7420 (0.86); 5.7285(0.44); 5.3676 (1.03); 5.3250 (2.60); 5.2642 (3.94); 5.2243 (2.34);5.2207 (2.27); 5.0140 (1.59); 5.0105 (1.62); 4.9877 (1.50); 4.9843(1.52); 4.5816 (0.47); 4.5687 (0.49); 4.5500 (1.39); 4.5367 (1.37);4.5208 (1.37); 4.5066 (1.34); 4.4889 (0.48); 4.4748 (0.47); 4.3923(0.71); 4.3596 (0.76); 4.0547 (0.87); 4.0369 (2.63); 4.0191 (2.70);4.0012 (1.40); 3.9622 (0.72); 3.7620 (1.05); 3.7309 (1.29); 3.7201(1.84); 3.6890 (1.47); 3.5752 (1.59); 3.5516 (1.58); 3.5332 (1.13);3.5097 (1.10); 3.4242 (0.83); 3.3788 (255.26); 3.3768 (255.06); 3.3727(209.45); 3.3699 (232.41); 3.3125 (1.04); 3.3074 (1.07); 3.2773 (1.18);3.2489 (0.69); 3.2435 (0.63); 2.8774 (0.54); 2.8465 (0.94); 2.8206(0.55); 2.6783 (0.38); 2.6737 (0.53); 2.6691 (0.39); 2.5271 (0.84);2.5224 (1.36); 2.5136 (27.60); 2.5092 (60.18); 2.5046 (80.99); 2.5000(57.47); 2.4955 (26.85); 2.3358 (0.40); 2.3313 (0.55); 2.3267 (0.40);2.2088 (16.00); 2.1502 (0.67); 2.1123 (1.37); 2.0865 (0.77); 2.0771(0.87); 1.9903 (12.30); 1.8314 (0.58); 1.8229 (0.64); 1.8004 (0.59);1.7919 (0.55); 1.5907 (0.55); 1.5814 (0.64); 1.5603 (0.59); 1.5511(0.58); 1.1921 (3.28); 1.1743 (6.54); 1.1565 (3.22); −0.0002 (4.51);

Ex. 51, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9706 (8.74); 7.3989 (0.78); 7.3817 (0.97); 7.3779 (1.64); 7.3609(1.66); 7.3571 (1.04); 7.3400 (0.84); 6.9372 (2.31); 6.9160 (2.12);6.8675 (1.21); 6.8422 (1.42); 6.8207 (1.13); 6.5037 (4.21); 6.1077(1.07); 6.0857 (1.30); 6.0770 (1.24); 6.0548 (1.13); 5.9293 (0.34);5.9160 (0.74); 5.9029 (0.73); 5.8895 (0.86); 5.8864 (0.53); 5.8729(0.95); 5.8596 (0.86); 5.8465 (0.92); 5.8334 (0.45); 5.3659 (1.00);5.3406 (1.76); 5.3366 (1.84); 5.3327 (0.85); 5.3235 (2.65); 5.3012(0.59); 5.2974 (1.51); 5.2933 (1.53); 5.2895 (0.62); 5.2665 (2.53);5.2239 (0.98); 5.2032 (0.61); 5.1221 (1.65); 5.1185 (1.63); 5.0957(1.55); 5.0922 (1.53); 4.5906 (1.63); 4.5869 (1.21); 4.5786 (2.74);4.5662 (1.56); 4.3942 (0.70); 4.3609 (0.75); 4.0550 (1.00); 4.0372(3.03); 4.0194 (3.09); 4.0015 (1.49); 3.9625 (0.71); 3.8005 (0.77);3.7702 (0.88); 3.7578 (1.10); 3.7280 (1.01); 3.5352 (1.27); 3.5132(1.28); 3.4928 (0.96); 3.4709 (0.98); 3.4237 (0.44); 3.4120 (0.35);3.4037 (0.62); 3.3943 (1.11); 3.3854 (0.68); 3.3772 (0.39); 3.3744(0.40); 3.3657 (0.78); 3.3620 (0.95); 3.3602 (0.99); 3.3556 (1.40);3.3418 (302.46); 3.3264 (1.23); 3.3180 (1.55); 3.3079 (0.78); 3.3038(0.71); 3.2744 (0.93); 3.2461 (0.52); 3.2401 (0.47); 3.0429 (1.33);2.8736 (0.50); 2.8543 (1.43); 2.8467 (0.90); 2.8166 (0.51); 2.6763(0.42); 2.6719 (0.59); 2.6673 (0.42); 2.5253 (0.96); 2.5206 (1.55);2.5119 (31.01); 2.5074 (66.11); 2.5029 (88.42); 2.4984 (62.76); 2.4940(29.40); 2.3344 (0.41); 2.3297 (0.58); 2.3251 (0.42); 2.2091 (16.00);2.1913 (1.25); 2.1498 (0.67); 2.1466 (0.63); 2.1125 (1.31); 2.0862(0.71); 2.0776 (0.71); 1.9900 (13.71); 1.8331 (0.55); 1.8264 (0.66);1.8031 (0.54); 1.7952 (0.52); 1.5914 (0.55); 1.5826 (0.61); 1.5608(0.58); 1.5508 (0.56); 1.2349 (0.34); 1.1921 (3.53); 1.1743 (7.13);1.1564 (3.43); 0.0081 (0.47); −0.0002 (15.63); −0.0084 (0.51);

Ex. 52, Solvent: DMSO, Spectrometer: 601.6 MHz

8.0358 (7.61); 7.2774 (0.74); 7.2742 (0.77); 7.2644 (0.94); 7.2612(1.03); 7.2580 (0.86); 7.2551 (0.81); 7.2446 (0.93); 7.2418 (0.95);7.1645 (0.94); 7.1617 (1.01); 7.1515 (2.51); 7.1487 (1.98); 7.1409(1.34); 7.1331 (1.26); 7.1279 (1.36); 7.1200 (1.37); 7.1150 (0.49);7.1069 (0.50); 6.5053 (4.35); 6.0851 (0.60); 6.0763 (0.47); 6.0669(0.85); 6.0568 (0.89); 6.0476 (0.52); 6.0393 (0.68); 6.0293 (0.35);5.9261 (1.26); 5.9136 (1.43); 5.9074 (1.36); 5.8949 (1.27); 5.3966(1.73); 5.3940 (1.69); 5.3915 (0.67); 5.3681 (1.60); 5.3654 (1.56);5.3630 (0.64); 5.3509 (1.29); 5.3225 (2.53); 5.2618 (2.61); 5.2407(1.82); 5.2382 (1.83); 5.2361 (1.33); 5.2336 (1.44); 5.2235 (1.62);4.6113 (2.93); 4.6016 (2.75); 4.3806 (0.76); 4.3588 (0.79); 4.0335(0.46); 4.0217 (0.46); 3.9801 (0.75); 3.9567 (0.77); 3.9224 (1.21);3.9035 (1.38); 3.8938 (1.51); 3.8750 (1.27); 3.3986 (0.64); 3.3926(0.49); 3.3855 (0.79); 3.3793 (1.41); 3.3493 (580.12); 3.3257 (12.73);3.3089 (1.64); 3.2826 (0.66); 3.2634 (1.08); 3.2439 (0.62); 3.2396(0.52); 2.8516 (0.54); 2.8309 (0.97); 2.8134 (0.56); 2.6178 (1.20);2.6149 (1.62); 2.6119 (1.14); 2.5426 (0.65); 2.5241 (2.96); 2.5211(4.06); 2.5179 (4.89); 2.5087 (96.04); 2.5061 (192.28); 2.5031 (255.09);2.5002 (185.23); 2.4804 (1.02); 2.4773 (0.92); 2.3903 (1.26); 2.3873(1.66); 2.3843 (1.20); 2.2055 (16.00); 2.1928 (0.47); 2.1259 (0.69);2.0981 (1.15); 2.0783 (2.81); 1.9905 (2.01); 1.8291 (0.33); 1.8150(0.64); 1.8090 (0.69); 1.7944 (0.66); 1.7890 (0.62); 1.5684 (0.65);1.5622 (0.69); 1.5482 (0.67); 1.5419 (0.64); 1.3969 (0.47); 1.2337(1.34); 1.1860 (0.57); 1.1741 (1.09); 1.1623 (0.56); 1.1365 (0.56);0.0052 (2.96); −0.0002 (72.51); −0.0057 (2.46);

Ex. 53, Solvent: DMSO, Spectrometer: 601.6 MHz

10.2595 (5.04); 8.0507 (7.33); 7.7701 (1.91); 7.7685 (2.00); 7.7574(2.47); 7.7558 (2.50); 7.6824 (0.70); 7.6738 (0.84); 7.6690 (1.38);7.6607 (1.40); 7.6562 (0.94); 7.6476 (0.77); 7.6120 (1.19); 7.5949(1.38); 7.5811 (0.83); 6.5807 (1.13); 6.5629 (1.65); 6.5441 (1.15);6.5072 (4.42); 5.3547 (1.33); 5.3263 (2.70); 5.2687 (2.59); 5.2404(1.30); 4.3893 (0.87); 4.3673 (0.90); 3.9893 (0.85); 3.9787 (1.05);3.9761 (1.10); 3.9663 (0.96); 3.9589 (1.23); 3.9501 (1.01); 3.9476(0.99); 3.9280 (0.85); 3.5858 (1.07); 3.5688 (1.10); 3.5567 (0.95);3.5400 (0.94); 3.4250 (0.34); 3.4189 (0.62); 3.4124 (0.47); 3.4059(0.76); 3.3998 (1.23); 3.3935 (0.82); 3.3865 (0.63); 3.3799 (1.01);3.3550 (256.99); 3.3314 (3.80); 3.2926 (0.68); 3.2728 (1.16); 3.2537(0.62); 3.2502 (0.55); 2.8615 (0.60); 2.8411 (1.10); 2.8235 (0.61);2.6182 (0.47); 2.6154 (0.64); 2.6125 (0.50); 2.5244 (1.20); 2.5214(1.70); 2.5065 (75.93); 2.5036 (101.45); 2.5007 (79.23); 2.3906 (0.48);2.3877 (0.64); 2.3850 (0.50); 2.2082 (16.00); 2.1456 (0.76); 2.1201(1.12); 2.0913 (0.88); 2.0788 (6.21); 1.8307 (0.72); 1.8107 (0.69);1.5836 (0.67); 1.5643 (0.66); 0.0049 (0.68); −0.0002 (13.17);

Ex. 54, Solvent: DMSO, Spectrometer: 601.6 MHz

8.7986 (0.80); 8.0657 (0.34); 8.0560 (7.35); 7.3883 (0.52); 7.3857(0.58); 7.3745 (1.21); 7.3720 (1.50); 7.3582 (1.39); 7.3556 (1.99);7.3466 (1.11); 7.3429 (1.41); 7.3341 (1.38); 7.3293 (0.67); 7.3204(0.56); 7.2762 (1.73); 7.2643 (1.25); 6.5057 (4.67); 5.8076 (1.23);5.7950 (1.39); 5.7886 (1.33); 5.7758 (1.19); 5.3525 (1.24); 5.3241(2.42); 5.2606 (2.46); 5.2323 (1.29); 4.3835 (0.74); 4.3617 (0.79);4.0454 (0.50); 4.0336 (1.54); 4.0217 (1.56); 4.0099 (0.53); 3.9806(0.75); 3.9577 (0.78); 3.9189 (1.07); 3.8997 (1.30); 3.8902 (1.38);3.8711 (1.15); 3.4091 (0.41); 3.4028 (0.65); 3.3964 (0.51); 3.3898(0.91); 3.3834 (1.46); 3.3753 (1.49); 3.3504 (474.54); 3.3268 (8.13);3.3000 (1.54); 3.2873 (1.89); 3.2713 (1.56); 3.2588 (1.98); 3.2438(0.60); 3.2396 (0.53); 2.8542 (0.55); 2.8505 (0.58); 2.8296 (1.00);2.8122 (0.55); 2.8083 (0.49); 2.6209 (0.40); 2.6179 (0.83); 2.6150(1.11); 2.6120 (0.79); 2.6090 (0.36); 2.5427 (0.68); 2.5242 (2.84);2.5212 (3.66); 2.5180 (4.29); 2.5092 (64.10); 2.5062 (130.48); 2.5032(174.29); 2.5002 (125.86); 2.4973 (57.51); 2.4799 (0.46); 2.4766 (0.46);2.4738 (0.44); 2.3933 (0.43); 2.3904 (0.86); 2.3874 (1.12); 2.3844(0.81); 2.3814 (0.39); 2.2201 (0.42); 2.2057 (16.00); 2.1901 (0.44);2.1246 (0.69); 2.0965 (1.20); 2.0782 (2.29); 2.0713 (0.77); 1.9905(6.90); 1.8821 (0.38); 1.8742 (0.72); 1.8695 (0.72); 1.8640 (0.95);1.8612 (1.12); 1.8566 (0.62); 1.8537 (0.68); 1.8502 (0.75); 1.8406(0.54); 1.8104 (0.60); 1.8039 (0.62); 1.7922 (0.72); 1.7867 (0.78);1.7849 (0.70); 1.7792 (0.77); 1.7736 (0.34); 1.7716 (0.49); 1.7660(0.46); 1.7354 (1.68); 1.5793 (0.35); 1.5662 (0.72); 1.5589 (0.80);1.5456 (0.75); 1.5391 (0.65); 1.3969 (0.44); 1.2338 (0.92); 1.1860(1.90); 1.1741 (3.78); 1.1623 (1.83); 1.0889 (0.49); 1.0841 (0.52);1.0818 (1.11); 1.0767 (1.64); 1.0716 (0.99); 1.0687 (1.20); 1.0636(1.59); 1.0587 (1.07); 1.0513 (0.99); 1.0481 (0.88); 1.0438 (1.23);1.0381 (1.09); 1.0305 (0.91); 1.0247 (0.56); 1.0183 (0.45); 1.0128(1.07); 1.0103 (0.64); 1.0053 (2.12); 1.0003 (1.42); 0.9975 (0.90);0.9918 (2.06); 0.9789 (1.26); 0.9693 (0.47); 0.9641 (0.41); 0.0052(1.72); −0.0002 (43.02); −0.0057 (1.34);

Ex. 55, Solvent: DMSO, Spectrometer: 399.95 MHz

7.9900 (5.11); 7.9528 (0.50); 7.3211 (0.55); 7.3176 (0.67); 7.2998(3.31); 7.2812 (2.93); 7.0705 (1.58); 7.0499 (1.35); 6.9729 (0.99);6.9546 (1.73); 6.9355 (0.83); 6.4972 (3.18); 5.8503 (0.83); 5.8310(0.97); 5.8223 (0.94); 5.8027 (0.85); 5.7551 (4.32); 5.3500 (0.66);5.3070 (1.88); 5.2535 (1.78); 5.2112 (0.63); 4.3837 (0.53); 4.3514(0.57); 4.1549 (1.74); 4.1435 (2.88); 4.1318 (1.83); 3.9877 (0.51);3.9499 (0.57); 3.8507 (0.85); 3.8225 (0.88); 3.8079 (1.06); 3.7800(0.93); 3.6311 (1.80); 3.6195 (2.15); 3.6085 (1.44); 3.4026 (0.53);3.3942 (0.34); 3.3750 (0.87); 3.3652 (0.66); 3.3274 (220.17); 3.2923(1.45); 3.2735 (1.17); 3.2628 (0.82); 3.2288 (16.00); 2.8907 (2.87);2.8654 (0.38); 2.8617 (0.39); 2.8323 (0.69); 2.8040 (0.40); 2.7315(2.65); 2.6709 (0.42); 2.5018 (70.79); 2.3284 (0.42); 2.2064 (11.12);2.1227 (0.49); 2.0958 (1.01); 2.0736 (0.61); 2.0630 (0.58); 1.9887(0.52); 1.8156 (0.47); 1.8063 (0.47); 1.7840 (0.43); 1.7776 (0.42);1.5733 (0.45); 1.5657 (0.46); 1.5433 (0.45); 1.5368 (0.43); 1.2357(0.62); −0.0002 (10.11); −0.0082 (0.34);

Ex. 56, Solvent: DMSO, Spectrometer: 399.95 MHz

8.7868 (0.75); 8.0463 (0.81); 8.0388 (8.80); 7.4462 (1.28); 7.4419(1.52); 7.4270 (1.61); 7.4229 (2.06); 7.4147 (0.94); 7.4104 (0.83);7.3957 (1.69); 7.3911 (1.41); 7.3761 (1.48); 7.3717 (1.20); 7.3397(0.34); 7.3110 (1.23); 7.3082 (1.42); 7.2922 (1.83); 7.2893 (1.97);7.2736 (0.78); 7.2706 (0.76); 7.1763 (2.17); 7.1735 (2.19); 7.1562(1.87); 7.1534 (1.78); 6.4972 (4.64); 5.7554 (11.20); 5.7402 (1.29);5.7311 (1.31); 5.7115 (1.10); 5.3515 (0.79); 5.3091 (2.37); 5.2551(2.53); 5.2130 (0.86); 4.3857 (0.69); 4.3536 (0.72); 4.0558 (0.33);4.0379 (1.00); 4.0201 (1.05); 4.0023 (0.53); 3.9867 (0.68); 3.9522(0.71); 3.8958 (1.11); 3.8672 (1.30); 3.8526 (1.44); 3.8241 (1.19);3.4178 (0.34); 3.4083 (0.53); 3.3985 (0.40); 3.3893 (0.64); 3.3796(1.07); 3.3705 (0.66); 3.3608 (0.54); 3.3515 (0.79); 3.3267 (95.06);3.3230 (198.62); 3.2903 (1.88); 3.2705 (1.95); 3.2471 (1.43); 3.2359(0.69); 3.2276 (1.64); 2.8628 (0.55); 2.8356 (0.90); 2.8060 (0.51);2.6750 (0.40); 2.6705 (0.54); 2.6658 (0.41); 2.5406 (0.34); 2.5238(0.95); 2.5191 (1.43); 2.5098 (30.88); 2.5057 (60.00); 2.5013 (83.80);2.4971 (58.45); 2.4928 (29.21); 2.3329 (0.41); 2.3281 (0.52); 2.3236(0.39); 2.2066 (16.00); 2.1936 (0.85); 2.1291 (0.65); 2.0990 (1.32);2.0734 (1.01); 1.9884 (4.67); 1.8725 (0.41); 1.8566 (0.73); 1.8468(0.87); 1.8412 (1.36); 1.8356 (0.87); 1.8301 (0.85); 1.8223 (0.97);1.8105 (0.93); 1.7848 (0.54); 1.5759 (0.57); 1.5668 (0.59); 1.5442(0.58); 1.5355 (0.54); 1.2344 (0.35); 1.1923 (1.29); 1.1745 (2.61);1.1567 (1.28); 1.0728 (0.54); 1.0647 (0.67); 1.0578 (0.73); 1.0521(1.19); 1.0467 (1.39); 1.0304 (2.30); 1.0194 (1.51); 1.0140 (2.46);1.0076 (1.75); 1.0021 (1.05); 0.9962 (0.99); 0.9871 (1.16); 0.9824(0.83); 0.9742 (0.89); 0.9631 (1.22); 0.9488 (0.63); 0.9430 (0.61);−0.0002 (3.06);

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and their relative intensities may be shownin comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of the 1H NMR spectra we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in the NMR peak lists.

The lists of the 1H NMR peaks are similar to the conventional 1H NMRprintouts and thus usually contain all peaks listed in conventional NMRinterpretations.

In addition, like conventional 1H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds, whichlikewise form part of the subject-matter of the invention, and/or peaksof impurities.

In the reporting of compound signals in the delta range of solventsand/or water, our lists of 1H NMR peaks show the usual solvent peaks,for example peaks of DMSO in DMSO-d₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help to identify reproductionof our preparation process with reference to “by-product fingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the relevant peak picking in conventional 1H NMRinterpretation.

Further details of 1H NMR peak lists can be found in Research DisclosureDatabase Number 564025.

Use Examples Example A Phytophthora Test (Tomato)/Protective

-   Solvent: 49 parts by weight of N,N-dimethylformamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective efficacy, young tomato plants are sprayed withthe active ingredient formulation at the stated application rate. 1 dayafter the treatment, the plants are inoculated with a spore suspensionof Phytophthora infestans, and then left to stand at 100% rel. humidityand 22° C. for 24 h. Subsequently, the plants are placed in a climatechamber at approx. 96% relative air humidity and a temperature ofapprox. 20° C.

Evaluation follows 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the control, whereas an efficacy of 100%means that no infection is observed.

In this test, the following inventive compounds show, at an activeingredient concentration of 100 ppm, an efficacy of 70% or more:

TABLE 2 Ex_no. Eff. % 1 100 2 100 3 100 4 95 5 95 6 95 7 100 8 100 9 9411 85 12 75 13 89 18 100 19 98 25 100 26 100 29 100 30 97 34 100 35 10036 100 37 94 38 94 39 94 40 100 41 98 41 97 42 94 43 97 44 94 45 100 46100 47 100 48 70 49 90 50 70 51 85 52 97 53 98 54 94 55 92 56 89

Example B Plasmopara Test (Grapevine)/Protective

-   Solvent: 24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable active ingredient formulation, 1 part by weight ofactive ingredient is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective efficacy, young plants are sprayed with theactive ingredient formulation at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Plasmopara viticola and then remain in an incubationcabin at approx. 20° C. and 100% relative air humidity for 1 day.Subsequently, the plants are placed in a greenhouse at approx. 21° C.and approx. 90% air humidity for 4 days. The plants are then moistenedand placed in an incubation cabin for 1 day.

Evaluation follows 6 days after the inoculation. 0% means an efficacywhich corresponds to that of the control, whereas an efficacy of 100%means that no infection is observed.

In this test, the following inventive compounds show, at an activeingredient concentration of 10 ppm, an efficacy of 70% or more:

TABLE 3 Ex_no. Eff. % 1 98 2 100 3 100 4 95 5 84 6 98 7 100 8 100 9 10011 100 12 100 13 100 16 96 17 92 18 95 19 98 25 100 29 100 30 100 34 8437 96 38 100 39 100 40 85 41 78 42 96 43 83 45 96 46 98 47 86 48 95 49100 50 100 51 100 52 98 53 100 54 91 55 93 56 98

1. A compound of formula (I)

wherein the radicals are each defined as follows: A is phenyl which maycontain up to five substituents, where the substituents are eachindependently selected from Z^(A-1), or A is an optionally benzofused,unsubstituted or substituted 5- or 6-membered heteroaryl optionallycomprising no more than four substituents, where the substituents oncarbon are each independently selected from Z^(A-2) and the substituentson nitrogen are each independently selected from Z^(A-3), Z^(A-1) arethe same or different and are each independently hydrogen, halogen,hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl,alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl,halocycloalkyl, halocycloalkenyl, hydroxyalkyl, cyanoalkyl, formylalkyl,alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl, alkynyloxyalkyl,alkylthioalkyl, alkylsulphinylalkyl, alkylaminoalkyl, halo alkylaminoalkyl, cycloalkylaminoalkyl, dialkylaminoalkyl, alkylcarbonylalkyl,alkylsulphonylalkyl, alkylcycloalkyl, alkylcycloalkenyl, alkoxy,alkylcycloalkylalkyl, halocycloalkoxy, alkylthio, haloalkylthio,cycloalkylthio, alkynylthio, alkenyloxy, alkynyloxy, haloalkoxy,haloalkenyloxy, haloalkynyloxy, cycloalkoxy, alkoxyalkoxy,cycloalkylalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonyloxy, cycloalkylamino, alkylcarbonylamino,cycloalkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino,haloalkylsulphonylamino, phenylsulphonylamino, cycloalkylalkyl,halocycloalkylalkyl, cycloalkylcycloalkyl, alkoxyalkoxyalkyl,alkylaminocarbonyloxy, alkylcarbonylalkoxy, cycloalkylaminocarbonyl,cycloalkylalkoxycarbonyl, alkylsulphinyl, haloalkylsulphinyl,alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcarbonyl,haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl,cycloalkoxycarbonyl, trialkylsilyl, —SF₅, phenyl, —C(═O)NR³R⁴ or —NR³R⁴,Z^(A-2) and R^(G1) are the same or different and are each independentlyhydrogen, halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH,alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl,cycloalkyl, halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl,alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl,alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy,haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino,phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl,cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy,—C(═O)NR³R⁴ or —NR³R⁴, Z^(A-3), R^(G2) and Z² are the same or differentand are each independently hydrogen, —C(═O)H, —C(═O)NR³R⁴, alkyl,alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, alkoxyalkyl,alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl,phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, cycloalkoxycarbonyl, phenyl or benzyl, R³ and R⁴ arethe same or different and are each independently hydrogen, alkyl,alkenyl, alkynyl, haloalkyl, cycloalkyl, benzyl or phenyl, L¹ isNR^(L12) or C(R^(L11))₂, R^(L11) is the same or different and isindependently hydrogen, halogen, hydroxyl, cyano, —C(═O)H, —C(═O)OH,alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl,alkoxyalkyl, alkylthioalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy,alkylthio, haloalkylthio, haloalkoxy, alkylcarbonyloxy,alkylcarbonylamino, alkylcarbonylthio, alkylsulphonyl,haloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,trialkylsilyloxy, —NR³R⁴ or —C(═O)NR³R⁴, or the two R^(L11) radicals,together with the carbon atom to which they are bonded, form acyclopropyl ring, or the two R^(L11) radicals are ═CH₂, ═COR³, ═NOR³ or═CHN(R⁷)₂, R^(L12) is hydrogen, —C(═O)H, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkylcycloalkyl, cycloalkylalkyl, cycloalkylaminocarbonyl,haloalkylaminocarbonyl, alkylsulphonyl, haloalkylsulphonyl,cycloalkylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, cycloalkoxycarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl, phenyl or benzyl, R⁷ is alkyl, alkenyl, alkynyl,haloalkyl, cycloalkyl, benzyl or phenyl, Y is sulphur or oxygen, X iscarbon or nitrogen, R² is hydrogen, alkyl, alkenyl, haloalkyl, alkoxy,halogen, cyano or hydroxyl, R¹⁰ is oxo, alkyl, alkenyl, haloalkyl,alkoxy, halogen, cyano or hydroxyl, P is 0, 1 or 2, G is 5-memberedheteroaryl which is substituted by Q and may otherwise be unsubstitutedor substituted, where the substituents on carbon are each independentlyselected from R^(G1) and the substituents on nitrogen are eachindependently selected from R^(G2), Q is saturated or partly or fullyunsaturated 5-membered heterocyclyl which is substituted by L²-R¹ andmay otherwise be unsubstituted or substituted, where the substituentsare each independently selected from R⁵, R⁵ is the same or different andis independently: bonded to carbon of the 5-membered heterocyclyl of Q:hydrogen, oxo, halogen, cyano, hydroxyl, nitro, —CHO, —C(═O)OH,—C(═O)NH₂, —C(═O)NR³R⁴, —NR³R⁴, alkyl, alkenyl, alkynyl, haloalkyl,haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl,cycloalkylalkyl, cycloalkylcycloalkyl, halocycloalkylalkyl,alkylcycloalkylalkyl, cycloalkenyl, halocycloalkenyl, alkoxyalkyl,haloalkoxyalkyl, cycloalkoxyalkyl, alkoxyalkoxyalkyl, alkylthioalkyl,formylalkyl, alkylcarbonylalkyl, alkylsulphinylalkyl,alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl,haloalkylaminoalkyl, cycloalkylaminoalkyl, alkylcarbonyl,haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl,cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl,hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy,cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio,cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl,haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl,alkylsulphonylamino, haloalkylsulphonylamino, bonded to nitrogen of the5-membered heterocyclyl of Q: hydrogen, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl,—C(═O)H, alkoxycarbonyl or alkylcarbonyl, L² is a direct bond, 0, C(═O),S(O)_(m), CHR²⁰ or NR²¹, m is 0, 1 or 2, R²⁰ is hydrogen, alkyl orhaloalkyl, R²¹ is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl,haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl, R¹ is phenylwhich is substituted once by a Z⁴ substituent and may additionallyoptionally have further substitution, where these additionalsubstituents are each independently selected from Z⁴ and Z¹, or R¹ isnaphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl,hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which issubstituted once by a Z⁵ substituent and may additionally optionallycomprise further substitution, where additional substituents are eachindependently selected from Z⁵ and Z¹, or R¹ is an optionallybenzofused, substituted 5- or 6-membered heteroaryl which is substitutedonce by a substituent, either on a carbon by Z⁶ or on a nitrogen by Z⁷,and may additionally optionally have further substitution, whereadditional substituents on carbon are each independently selected fromZ¹ and Z⁶, and the additional substituents on nitrogen are eachindependently selected from Z² and Z⁷, Z¹ is hydrogen, halogen,hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl,hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl,alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio,haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy,alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy,haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR³R⁴, —NR³R⁴, or-L³Z³, L³ is a direct bond, —CH₂—, —C(═O)—, sulphur, oxygen, —C(═O)O—,—C(═O)NH—, —OC(═O)— or —NHC(═O)—, Z³ is a phenyl radical, naphthalenylradical or a 5- or 6-membered heteroaryl radical, each of which maycontain 0, 1, 2 or 3 substituents, where the substituents are eachindependently selected from the following list: substituents on carbon:halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy,haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy,alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,trisilylalkyl or phenyl, substituents on nitrogen: hydrogen, —C(═O)H,alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl,cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl,alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl,phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, cycloalkoxycarbonyl, —C(═O)NR³R⁴, phenyl or benzyl,Z⁴ is SH, C(═O)H, C₇-C₈-cycloalkyl, C₇-C₈-halocycloalkyl,cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl,halocycloalkenyl, C₄-C₆-alkoxy-C₁-C₄-alkyl, C₃-alkoxy-C₂-C₄-alkyl,alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl,alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C₄-C₆-alkylcarbonyl,haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl,C₅-C₆-hydroxyalkyl, C₅-C₆-alkoxy, C₅-C₆-haloalkoxy, cycloalkoxy,halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy,alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy,haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy,C₅-C₆-alkylthio, C₅-C₆-haloalkylthio, C₅-C₆-alkylsulphinyl,C₅-C₆-haloalkylsulphinyl, C₅-C₆-alkylsulphonyl,C₅-C₆-haloalkylsulphonyl, cycloalkylsulphonyl, tri(C₃-C₄-alkyl)silyl,alkylsulphonylamino or haloalkylsulphonylamino, Z⁵ istri(C₂-C₄-alkyl)silyl, benzyl, phenyl, SH, C₅-C₆-alkoxy,C₅-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₅-C₆-alkylthio orC₅-C₆-haloalkylthio, Z⁶ is SH, cycloalkylcycloalkyl ortri(C₃-C₄-alkyl)silyl, Z⁷ is alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl,cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl orphenyl, and/or a salt, metal complex and/or an N-oxide thereof, with theproviso that the following compounds are excluded:

in which the symbols are each defined as follows: Y is oxygen orsulphur, R² is hydrogen or halogen, Q is

R⁵ is hydrogen, cyano, C₁-C₃-alkyl or C₁-C₃-haloalkyl, L² is a directbond and R1 is as defined above, wherein, when R1 is substituted phenyl,naphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl,hexahydronaphthalenyl, octahydronaphthalenyl or indenyl or an optionallybenzofused, 5- or 6-membered heteroaryl, not more than two substituentsare present on the carbocycles or heterocycles mentioned.
 2. Thecompound of formula (I) and/or salt, metal complex and/or an N-oxidethereof according to claim 1, wherein the radical definitions are asfollows: A is phenyl which optionally comprise no more than twosubstituents, where the substituents are each independently selectedfrom the following list: halogen, cyano, hydroxyl, —NR³R⁴, —C(═O)NR³R⁴,nitro, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkenyloxy,C₁-C₄-alkynyloxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphonyl, C₁-C₄-alkoxy-C₁-C₆-alkyl,hydroxy-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₁-C₆-alkylcarbonyloxy or —C(═O)H, or A is a heteroaromatic radicalselected from the following group: furan-2-yl, furan-3-yl,thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl,isoxazol-5-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, oxazol-2-yl,oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-1-yl,pyrazol-3-yl, pyrazol-4-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl,1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, pyridin-2-yl, pyridin-3-yl,pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrazin-2-yl,pyrazin-3-yl, pyrimidin-2-yl, pyrimidin-4-yl or pyrimidin-5-yl whichoptionally comprise no more than two substituents, where thesubstituents are each independently selected from the following list:substituents on carbon: halogen, cyano, hydroxyl, nitro, —NR³R⁴,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulphonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulphonyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbonyloxy or phenyl, substituents onnitrogen: C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₁₀-cycloalkyl-C₁-C₆-alkyl,C₁-C₆-haloalkylcarbonyl, phenyl, benzyl, C₁-C₄-alkylsulphonyl,C₁-C₄-haloalkylsulphonyl, phenylsulphonyl, —C(═O)H, orC₁-C₆-alkylcarbonyl, L¹ is CHR^(L11) or NR^(L12), R^(L11) is hydrogen,methyl, ethyl or cyclopropyl, R^(L12) is hydrogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₃-C₈-cycloalkyl, C₁-C₄-alkylsulphonyl,C₁-C₄-alkoxycarbonyl, Y is oxygen, X is carbon, R² is hydrogen,fluorine, chlorine, bromine or hydroxyl, R¹⁰ is oxo, C₁-C₄-alkyl,C₁-C₄-alkenyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, halogen, cyano orhydroxyl, p is 0 or 1, G is

where the bond identified by “v” is bonded directly to X and where thebond identified by “w” is bonded directly to Q, R^(G1) is hydrogen orhalogen, Q is

where the bond identified by “*” is bonded directly to G, and where thebond identified by “#” is bonded directly to L², or where the bondidentified by “*” is bonded directly to L², and where the bondidentified by “#” is bonded directly to G, R⁵ is the same or differentand is independently: bonded to carbon of the 5-membered heterocyclyl ofQ: hydrogen, cyano, —NR³R⁴, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl, C₃-C₈-halocycloalkyl,C₁-C₄-alkyl-C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₈-cycloalkoxy-C₁-C₄-alkyl,C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₈-cycloalkoxy,C₃-C₈-halocycloalkoxy, C₃-C₈-cycloalkyl-C₁-C₄-alkoxy, C₂-C₆-alkenyloxy,C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-haloalkynyloxy,C₁-C₆-alkoxy-C₁-C₄-alkoxy, C₁-C₆-alkylcarbonyloxy,C₁-C₆-haloalkylcarbonyloxy, C₃-C₈-cycloalkylcarbonyloxy,C₁-C₆-alkylcarbonyl-C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio,C₃-C₈-cycloalkylthio, bonded to nitrogen of the 5-membered heterocyclylof Q: hydrogen, —C(═O)H, C₁-C₃-alkyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl or benzyl, L² is a direct bond, —C(═O)—, —CHR²⁰— or—NR²¹—, R²⁰ is hydrogen, methyl, ethyl, trifluoromethyl, R²¹ is hydrogenor methyl, R¹ is phenyl which is substituted once by a Z⁴ substituentand may additionally optionally comprise further substitution, whereadditional substituents are each independently selected from Z⁴ and Z¹⁻¹or R¹ is naphthalen-1-yl, naphthalen-2-yl,1,2,3,4-tetrahydronaphthalen-1-yl, 1,2,3,4-tetrahydronaphthalen-2-yl,5,6,7,8-tetrahydronaphthalen-1-yl, 5,6,7,8-tetrahydronaphthalen-2-yl,decalin-1-yl, decalin-2-yl, 1H-inden-1-yl, 2,3-dihydro-1H-inden-1-yl,1H-inden-2-yl, 1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl,1H-inden-6-yl, 1H-inden-7-yl, indan-1-yl, indan-2-yl, indan-3-yl,indan-4-yl or indan-5-yl, where each is substituted once by a Z⁵substituent and may additionally optionally comprise furthersubstitution, where additional substituents are each independentlyselected from Z⁵ and Z¹⁻², or R¹ is a 5- or 6-membered heteroarylradical which is substituted once by a substituent, either on a carbonby Z⁶ or on a nitrogen by Z⁷, and may additionally optionally comprisefurther substitution, where additional substituents on carbon are eachindependently selected from Z¹⁻³ and Z⁶, and additional substituents onnitrogen are each independently selected from Z², or R¹ is benzofusedsubstituted 5- or 6-membered heteroaryl which is substituted by one Z⁴substituent and may additionally optionally comprise furthersubstitution, where additional substituents on carbon are eachindependently selected from Z¹⁻², and additional substituents onnitrogen are each independently selected from Z², Z¹⁻¹ is hydrogen,halogen, cyano, hydroxyl, nitro, —C(═O)NR³R⁴, —NR³R⁴, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,C₂-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₈-halocycloalkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, C₃-C₆-cycloalkylthio or -L³Z³, Z¹⁻² are the same ordifferent and are each independently hydrogen, halogen, cyano, nitro,—NR³R⁴, —C(═O)NR³R⁴, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-alkoxycarbonyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkylcarbonylthio,C₁-C₄-alkylthio or C₁-C₄-haloalkylthio, Z¹⁻³ is hydrogen, halogen,cyano, hydroxyl, nitro, —C(═O)NR³R⁴, —NR³R⁴, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkylthio,C₁-C₆-haloalkylthio or C₃-C₆-cycloalkylthio, Z² is the same or differentand is independently hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl, C₁-C₄-haloalkylsulphonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl, phenylsulphonyl,C₁-C₄-alkylsulphonyl, —C(═O)H, C₁-C₃-haloalkylcarbonyl orC₁-C₃-alkylcarbonyl, L³ is a direct bond, —CH₂—, sulphur, oxygen, Z³ isa phenyl radical, naphthalenyl or a 5- or 6-membered heteroaryl radicalwhich optionally comprise no more than contain up to two substituents,where the substituents are each independently selected from thefollowing list: substituents on carbon: halogen, cyano, nitro, hydroxyl,amino, —SH, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-haloalkyl,C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₂-C₄-alkoxyalkyl,C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylsulphonyl, C_(r)C₄-haloalkylsulphonyl or C₁-C₄-alkylamino, di(C₁-C₄-alkyl)amino,substituents on nitrogen: C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl, C₁-C₄-haloalkylsulphonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-haloalkoxycarbonyl, phenylsulphonyl,C₁-C₄-alkylsulphonyl, —C(═O)H, or C₁-C₃-alkylcarbonyl, Z⁴ is C(═O)H,C₇-C₈-cycloalkyl, C₃-C₆-cycloalkyl-C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl,C₄-C₆-alkoxy-C₁-C₄-alkyl, C₄-C₆-alkoxy-C₁-C₄-alkyl,C₃-alkoxy-C₂-C₄-alkyl, C₁-C₃-alkoxy-C₂-C₃-alkoxy-C₁-C₃-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, C₁-C₄-alkylsulphinyl-C₁-C₂-alkyl,C₁-C₄-alkylsulphonyl-C₁-C₂-alkyl, C₁-C₄-alkylamino-C₁-C₂-alkyl,C₁-C₂-dialkylamino-C₁-C₂-alkyl, C₁-C₄-haloalkylamino-C₁-C₂-alkyl,C₃-C₆-cycloalkylamino-C₁-C₂-alkyl, C₄-C₆-alkylcarbonyl,C₁-C₄-haloalkylcarbonyl, C₃-C₆-cycloalkylcarbonyl,C₃-C₆-cycloalkoxycarbonyl, C₃-C₆-cycloalkyl-C₁-C₂-alkoxycarbonyl,C₃-C₆-cycloalkylaminocarbonyl, C₁-C₄-haloalkoxy-C₁-C₂-alkyl,C₅-C₆-hydroxyalkyl, C₅-C₆-alkoxy, C₅-C₆-haloalkoxy, C₃-C₆-cycloalkoxy,C₃-C₆-halocycloalkoxy, C₃-C₆-cycloalkylalkoxy, C₂-C₆-alkenyloxy,C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-haloalkynyloxy,C₁-C₄-alkoxy-C₁-C₄-alkoxy, cyano-C₁-C₄-alkoxy,C₁-C₄-haloalkylcarbonyloxy, C₃-C₆-cycloalkylcarbonyloxy,C₁-C₄-alkylcarbonyl-C₁-C₄-alkoxy, C₅-C₆-alkylthio, C₅-C₆-haloalkylthio,C₅-C₆-alkylsulphinyl, C₅-C₆-haloalkylsulphinyl, C₅-C₆-alkylsulphonyl,C₅-C₆-haloalkylsulphonyl, C₃-C₆-cycloalkylsulphonyl,tri(C₃-C₄-alkyl)silyl, C₁-C₄-alkylsulphonylamino orC₁-C₄-haloalkylsulphonylamino, Z⁵ is benzyl, phenyl, C₂-C₆-alkenyloxy,C₂-C₆-alkynyloxy, C₅-C₆-alkylthio or C₅-C₆-haloalkylthio, Z⁶ isC₃-C₆-cycloalkylcyclopropyl, C₃-C₆-cycloalkylcyclohexyl ortri(C₃-C₄-alkyl)silyl, Z⁷ is C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkyl-C₃-C₆-cycloalkyl,C₃-C₆-cycloalkylcyclopropyl, C₃-C₆-cycloalkylcyclohexyl,cycloalkylalkyl, C₁-C₄-alkylsulphonyl, C(═O)H, benzyl or phenyl.
 3. Thecompound of formula (I) and/or salt, metal complex and/or an N-oxidethereof according to claim 1, wherein the radical definitions are eachas follows: A is phenyl which optionally comprise no more than twosubstituents, where the substituents are each independently selectedfrom the following list: methyl, ethyl, iodine, chlorine, bromine,fluorine, methoxy, ethoxy, difluoromethyl or trifluoromethyl or A ispyrazol-1-yl which optionally comprise no more than two substituents,where the substituents are each independently selected from thefollowing list: methyl, ethyl, chlorine, bromine, fluorine ortrifluoromethyl.
 4. The compound of formula (I) and/or salt, metalcomplex and/or an N-oxide thereof according to claim 1, wherein theradical definitions are each as follows: G is G¹, G² or G³, R^(G1) ishydrogen.
 5. The compound of formula (I) and/or salt, metal complexand/or an N-oxide thereof according to claim 1, wherein the radicaldefinitions are each as follows: Q is

where the bond identified by “x” is bonded directly to G, and the bondidentified by “y” is bonded directly to L².
 6. The compound of theformula (I) and/or salt, metal complex and/or an N-oxide thereofaccording to claim 1, wherein the radical definitions are each asfollows: R¹ is phenyl which optionally comprise no more than 3substituents, where one substituent is selected from Z⁴ and any furthersubstituents are selected from the following list: fluorine, chlorine,bromine, iodine, cyano, nitro, hydroxyl, amino, —SH, —C(═O)H, methyl,ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl,1,2-dimethylethyl, ethenyl, ethynyl, trifluoromethyl, difluoromethyl,trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy,n-propoxy, 1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl,ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,n-propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl,1-ethenyloxy, 2-propenyloxy, 2-propynyloxy, methylcarbonyloxy,trifluoroalkylcarbonyloxy, chloromethylcarbonyloxy, methylthio,ethylthio, methylsulphonyl, methylsulphonylamino,trifluoromethylsulphonylamino or -L³R³, or R¹ is naphthalen-1-yl,naphthalen-2-yl, 1,2,3,4-tetrahydronaphthalen-1-yl,1,2,3,4-tetrahydronaphthalen-2-yl, 5,6,7,8-tetrahydronaphthalen-1-yl,5,6,7,8-tetrahydronaphthalen-2-yl, decalin-1-yl, decalin-2-yl,1H-inden-1-yl, 2,3-dihydro-1H-inden-1-yl, 1H-inden-2-yl, 1H-inden-3-yl,1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl, 1H-inden-7-yl, indan-1-yl,indan-2-yl, indan-3-yl, indan-4-yl or indan-5-yl, where these are eachsubstituted at least once by a Z⁵ substituent and may optionallyadditionally comprise further substitution, where the additionalsubstituents are each independently selected from Z⁵ and the groupconsisting of methyl, methoxy, cyano, fluorine, chlorine, bromine andiodine, or R¹ is furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl,isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, pyrrol-1-yl, pyrrol-2-yl,pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl,thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl,isothiazol-5-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl,imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-triazol-1-yl,1,2,3-triazol-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-1-yl,1,2,4-triazol-3-yl, 1,2,4-triazol-4-yl, pyridin-2-yl, pyridin-3-yl,pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl,pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl, each of which maycontain 1 or 2 substituent(s), where one substituent is either on acarbon and is selected from Z⁶ or is on a nitrogen and is selected fromZ⁷, and any further substituent is selected from the following list:substituents on carbon: fluorine, chlorine, bromine, iodine, cyano,nitro, hydroxyl, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl,1,1-dimethylethyl, 1,2-dimethylethyl, ethenyl, ethynyl, trifluoromethyl,difluoromethyl, trichloromethyl, dichloromethyl, cyclopropyl, methoxy,ethoxy, n-propoxy, 1-methylethoxy, 1,1-dimethylethoxy, methylcarbonyl,ethylcarbonyl, trifluoromethylcarbonyl, methoxycarbonyl, ethoxycarbonyl,n-propoxycarbonyl, 1-methylethoxycarbonyl, 1,1-dimethylethoxycarbonyl,1-ethenyloxy, 2-propenyloxy, 2-propinyloxy, methylcarbonyloxy,trifluoroalkylcarbonyloxy, chloromethylcarbonyloxy, methylcarbonylamino,trifluoroalkylcarbonylamino, chloromethylcarbonylamino, methylthio,ethylthio, methylsulphinyl, methylsulphonyl, methylsulphonyloxy,trifluoroalkylsulphonyloxy, methylsulphonylamino ortrifluoromethylsulphonylamino, substituents on nitrogen: methyl, ethyl,n-propyl, —C(═O)H, methylcarbonyl, trifluoromethylcarbonyl,chloromethylcarbonyl, methylsulphonyl, trifluoromethylsulphonyl,phenylsulphonyl, phenyl or 2-propynyl, or R¹ is indol-1-yl, indol-2-yl,indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl,benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl,benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl,indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl,1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl,1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl,1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl,1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl,1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl,1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl,1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl,1,3-benzoxazol-7-yl, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl,quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl,isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl,isoquinolin-6-yl, isoquinolin-7-yl or isoquinolin-8-yl, which issubstituted by a substituent, either on a carbon by Z⁶ or on a nitrogenby Z⁷, and additionally optionally bears a further substituent selectedfrom the following list: substituents on carbon: fluorine, chlorine,bromine, iodine, methyl, methoxy, substituents on nitrogen: methyl,ethyl, n-propyl, —C(═O)H, methylcarbonyl, trifluoromethylcarbonyl,chloromethylcarbonyl, methylsulphonyl, trifluoromethylsulphonyl,phenylsulphonyl, phenyl or 2-propynyl.
 7. The compound of formula (I)and/or salt, metal complex and/or an N-oxide thereof according to claim1, wherein the radical definitions are each as follows: G is G¹.
 8. Acompound of formula (VII)

and/or a salt, metal complex and/or N-oxides thereof, wherein R^(G1) arethe same or different and are each independently hydrogen, halogen,hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl,alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl,alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl,alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy,haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino,phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl,cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy,—C(═O)NR³R⁴ or —NR³R⁴, R³ and R⁴ are the same or different and are eachindependently hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl,benzyl or phenyl, X is carbon or nitrogen, R² is hydrogen, alkyl,alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, R¹⁰ is oxo,alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, p is 0, 1or 2, G is 5-membered heteroaryl which is substituted by Q and mayotherwise be unsubstituted or substituted, where the substituents oncarbon are each independently selected from R^(G1) and the substituentson nitrogen are each independently selected from R^(G2), Q is saturatedor partly or fully unsaturated 5-membered heterocyclyl which issubstituted by L²-R¹ and may otherwise be unsubstituted or substituted,where the substituents are each independently selected from R⁵, R⁵ isthe same or different and is independently: bonded to carbon of the5-membered heterocyclyl of Q: hydrogen, oxo, halogen, cyano, hydroxyl,nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —C(═O)NR³R⁴, —NR³R⁴, alkyl, alkenyl,alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl,halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl,halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl,alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl,alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl,dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl,alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl,cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl,hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy,cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio,cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl,haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl,alkylsulphonylamino, haloalkylsulphonylamino, bonded to nitrogen of the5-membered heterocyclyl of Q: hydrogen, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl,—C(═O)H, alkoxycarbonyl or alkylcarbonyl, L² is a direct bond, 0, C(═O),S(O)_(m), CHR²⁰ or NR²¹, m is 0, 1 or 2, R²⁰ is hydrogen, alkyl orhaloalkyl, R²¹ is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl,haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl, R¹ is phenylwhich is substituted once by a Z⁴ substituent and may additionallyoptionally have further substitution, where these additionalsubstituents are each independently selected from Z⁴ and Z¹, or R¹ isnaphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl,hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which issubstituted once by a Z⁵ substituent and may additionally optionallycomprise further substitution, where additional substituents are eachindependently selected from Z⁵ and Z¹, or R¹ is an optionallybenzofused, substituted 5- or 6-membered heteroaryl which is substitutedonce by a substituent, either on a carbon by Z⁶ or on a nitrogen by Z⁷,and may additionally optionally have further substitution, whereadditional substituents on carbon are each independently selected fromZ¹ and Z⁶, and the additional substituents on nitrogen are eachindependently selected from Z² and Z⁷, Z¹ is hydrogen, halogen,hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl,hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl,alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio,haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy,alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy,haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR³R⁴, —NR³R⁴, or-L³Z³, L³ is a direct bond, —CH₂—, —C(═O)—, sulphur, oxygen, —C(═O)O—,—C(═O)NH—, —OC(═O)— or —NHC(═O)—, Z³ is a phenyl radical, naphthalenylradical or a 5- or 6-membered heteroaryl radical, each of which maycontain 0, 1, 2 or 3 substituents, where the substituents are eachindependently selected from the following list: substituents on carbon:halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy,haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy,alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,trisilylalkyl or phenyl, substituents on nitrogen: hydrogen, —C(═O)H,alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl,cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl,alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl,phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, cycloalkoxycarbonyl, —C(═O)NR³R⁴, phenyl or benzyl,Z⁴ is SH, C(═O)H, C₇-C₈-cycloalkyl, C₇-C₈-halocycloalkyl,cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl,halocycloalkenyl, C₄-C₆-alkoxy-C₁-C₄-alkyl, C₃-alkoxy-C₂-C₄-alkyl,alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl,alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C₄-C₆-alkylcarbonyl,haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl,C₅-C₆-hydroxyalkyl, C₅-C₆-alkoxy, C₅-C₆-haloalkoxy, cycloalkoxy,halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy,alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy,haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy,C₅-C₆-alkylthio, C₅-C₆-haloalkylthio, C₅-C₆-alkylsulphinyl,C₅-C₆-haloalkylsulphinyl, C₅-C₆-alkylsulphonyl,C₅-C₆-haloalkylsulphonyl, cycloalkylsulphonyl, tri(C₃-C₄-alkyl)silyl,alkylsulphonylamino or haloalkylsulphonylamino, Z⁵ istri(C₂-C₄-alkyl)silyl, benzyl, phenyl, SH, C₅-C₆-alkoxy,C₅-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₅-C₆-alkylthio orC₅-C₆-haloalkylthio, Z⁶ is SH, cycloalkylcycloalkyl ortri(C₃-C₄-alkyl)silyl, Z⁷ is alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl,cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl orphenyl, and W¹³ is a leaving group.
 9. A compound of formula (XVIId)

and/or a salt, metal complex and/or N-oxide thereof, wherein the symbolW⁶ is acetyl, C₁-C₄ alkoxycarbonyl, benzyl or benzyloxycarbonyl andR^(G1) are the same or different and are each independently hydrogen,halogen, hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl,alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl,alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl,alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy,haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino,phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl,cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy,—C(═O)NR³R⁴ or —NR³R⁴, X is carbon or nitrogen, R² is hydrogen, alkyl,alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, R¹⁰ is oxo,alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, P is 0, 1or 2, G is 5-membered heteroaryl which is substituted by Q and mayotherwise be unsubstituted or substituted, where the substituents oncarbon are each independently selected from R^(G1) and the substituentson nitrogen are each independently selected from R^(G2), Q is saturatedor partly or fully unsaturated 5-membered heterocyclyl which issubstituted by L²-R¹ and may otherwise be unsubstituted or substituted,where the substituents are each independently selected from R⁵, R⁵ isthe same or different and is independently: bonded to carbon of the5-membered heterocyclyl of Q: hydrogen, oxo, halogen, cyano, hydroxyl,nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —C(═O)NR³R⁴, —NR³R⁴, alkyl, alkenyl,alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl,halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl,halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl,alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl,alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl,dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl,alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl,cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl,hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy,cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio,cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl,haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl,alkylsulphonylamino, haloalkylsulphonylamino, bonded to nitrogen of the5-membered heterocyclyl of Q: hydrogen, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl,—C(═O)H, alkoxycarbonyl or alkylcarbonyl, L² is a direct bond, O, C(═O),S(O)_(m), CHR²⁰ or NR²¹, m is 0, 1 or 2, R²⁰ is hydrogen, alkyl orhaloalkyl, R²¹ is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl,haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl, R¹ is phenylwhich is substituted once by a Z⁴ substituent and may additionallyoptionally have further substitution, where these additionalsubstituents are each independently selected from Z⁴ and Z¹, or R¹ isnaphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl,hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which issubstituted once by a Z⁵ substituent and may additionally optionally hawcomprise further substitution, where additional substituents are eachindependently selected from Z⁵ and Z¹, or R¹ is an optionallybenzofused, substituted 5- or 6-membered heteroaryl which is substitutedonce by a substituent, either on a carbon by Z⁶ or on a nitrogen by Z⁷,and may additionally optionally have further substitution, whereadditional substituents on carbon are each independently selected fromZ¹ and Z⁶, and the additional substituents on nitrogen are eachindependently selected from Z² and Z⁷, Z¹ is hydrogen, halogen,hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl,hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl,alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio,haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy,alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy,haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR³R⁴, —NR³R⁴, or-L³Z³, L³ is a direct bond, —CH₂—, —C(═O)—, sulphur, oxygen, —C(═O)O—,—C(═O)NH—, —OC(═O)— or —NHC(═O)—, Z³ is a phenyl radical, naphthalenylradical or a 5- or 6-membered heteroaryl radical, each of which maycontain 0, 1, 2 or 3 substituents, where the substituents are eachindependently selected from the following list: substituents on carbon:halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy,haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy,alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,trisilylalkyl or phenyl, substituents on nitrogen: hydrogen, —C(═O)H,alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl,cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl,alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl,phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, cycloalkoxycarbonyl, —C(═O)NR³R⁴, phenyl or benzyl,Z⁴ is SH, C(═O)H, C₇-C₈-cycloalkyl, C₇-C₈-halocycloalkyl,cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl,halocycloalkenyl, C₄-C₆-alkoxy-C₁-C₄-alkyl, C₃-alkoxy-C₂-C₄-alkyl,alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl,alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C₄-C₆-alkylcarbonyl,haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl,C₅-C₆-hydroxyalkyl, C₅-C₆-alkoxy, C₅-C₆-haloalkoxy, cycloalkoxy,halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy,alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy,haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy,C₅-C₆-alkylthio, C₅-C₆-haloalkylthio, C₅-C₆-alkylsulphinyl,C₅-C₆-haloalkylsulphinyl, C₅-C₆-alkylsulphonyl,C₅-C₆-haloalkylsulphonyl, cycloalkylsulphonyl, tri(C₃-C₄-alkyl)silyl,alkylsulphonylamino or haloalkylsulphonylamino, Z⁵ istri(C₂-C₄-alkyl)silyl, benzyl, phenyl, SH, C₅-C₆-alkoxy,C₅-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₅-C₆-alkylthio orC₅-C₆-haloalkylthio, Z⁶ is SH, cycloalkylcycloalkyl ortri(C₃-C₄-alkyl)silyl, Z⁷ is alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl,cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl orphenyl.
 10. A compound of formula (XIIIa)

and/or a salt, metal complex and/or N-oxide thereof, wherein R^(G1) arethe same or different and are each independently hydrogen, halogen,hydroxyl, thioxyl, nitro, cyano, —C(═O)H, —C(═O)OH, alkyl, alkenyl,alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,halocycloalkyl, hydroxyalkyl, formylalkyl, alkoxyalkyl,alkylcarbonylalkyl, alkylcycloalkyl, alkoxy, alkylcycloalkylalkyl,alkylthio, haloalkylthio, alkynylthio, alkenyloxy, alkynyloxy,haloalkoxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonylamino, alkylsulphonylamino, haloalkylsulphonylamino,phenylsulphonylamino, cycloalkylalkyl, halocycloalkylalkyl,cycloalkylcycloalkyl, alkoxycarbonyloxy, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyloxy,—C(═O)NR³R⁴ or —NR³R⁴, X is carbon or nitrogen, R² is hydrogen, alkyl,alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, R¹⁰ is oxo,alkyl, alkenyl, haloalkyl, alkoxy, halogen, cyano or hydroxyl, P is 0, 1or 2, G is 5-membered heteroaryl which is substituted by Q and mayotherwise be unsubstituted or substituted, where the substituents oncarbon are each independently selected from R^(G1) and the substituentson nitrogen are each independently selected from R^(G2), Q is saturatedor partly or fully unsaturated 5-membered heterocyclyl which issubstituted by L²-R¹ and may otherwise be unsubstituted or substituted,where the substituents are each independently selected from R⁵, R⁵ isthe same or different and is independently: bonded to carbon of the5-membered heterocyclyl of Q: hydrogen, oxo, halogen, cyano, hydroxyl,nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —C(═O)NR³R⁴, —NR³R⁴, alkyl, alkenyl,alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl,halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl, cycloalkylcycloalkyl,halocycloalkylalkyl, alkylcycloalkylalkyl, cycloalkenyl,halocycloalkenyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkoxyalkyl,alkoxyalkoxyalkyl, alkylthioalkyl, formylalkyl, alkylcarbonylalkyl,alkylsulphinylalkyl, alkylsulphonylalkyl, alkylaminoalkyl,dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl,alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkoxycarbonyl,cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl,hydroxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, halocycloalkoxy,cycloalkylalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy,haloalkynyloxy, alkoxyalkoxy, alkylcarbonyloxy, haloalkylcarbonyloxy,cycloalkylcarbonyloxy, alkylcarbonylalkoxy, alkylthio, haloalkylthio,cycloalkylthio, alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl,haloalkylsulphonyl, cycloalkylsulphonyl, trialkylsilyl,alkylsulphonylamino, haloalkylsulphonylamino, bonded to nitrogen of the5-membered heterocyclyl of Q: hydrogen, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkylcycloalkyl, cycloalkylalkyl, phenyl, benzyl, alkylsulphonyl,—C(═O)H, alkoxycarbonyl or alkylcarbonyl, L² is a direct bond, 0, C(═O),S(O)_(m), CHR²⁰ or NR²¹, m is 0, 1 or 2, R²⁰ is hydrogen, alkyl orhaloalkyl, R²¹ is hydrogen, alkyl, haloalkyl, cycloalkyl, alkylcarbonyl,haloalkylcarbonyl, alkoxycarbonyl or haloalkoxycarbonyl, R¹ is phenylwhich is substituted once by a Z⁴ substituent and may additionallyoptionally have further substitution, where these additionalsubstituents are each independently selected from Z⁴ and Z¹, or R¹ isnaphthyl, dihydronaphthalenyl, tetrahydronaphthalenyl,hexahydronaphthalenyl, octahydronaphthalenyl or indenyl which issubstituted once by a Z⁵ substituent and may additionally optionallycomprise further substitution, where additional substituents are eachindependently selected from Z⁵ and Z¹, or R¹ is an optionallybenzofused, substituted 5- or 6-membered heteroaryl which is substitutedonce by a substituent, either on a carbon by Z⁶ or on a nitrogen by Z⁷,and may additionally optionally have further substitution, whereadditional substituents on carbon are each independently selected fromZ¹ and Z⁶, and the additional substituents on nitrogen are eachindependently selected from Z² and Z⁷, Z¹ is hydrogen, halogen,hydroxyl, nitro, cyano, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkoxy, alkoxyalkyl,hydroxyalkyl, haloalkoxy, alkylcarbonyl, alkoxycarbonyl,alkylcycloalkyl, cycloalkoxyalkyl, cycloalkylamino, alkylthio,haloalkylthio, cycloalkylthio, cycloalkylalkyl, alkylcarbonyloxy,alkylcarbonylamino, haloalkylcarbonylamino, alkylcarbonylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyloxy,haloalkylsulphonyloxy, alkylcycloalkylalkyl, —C(═O)NR³R⁴, —NR³R⁴, or-L³Z³, L³ is a direct bond, —CH₂—, —C(═O)—, sulphur, oxygen, —C(═O)O—,—C(═O)NH—, —OC(═O)— or —NHC(═O)—, Z³ is a phenyl radical, naphthalenylradical or a 5- or 6-membered heteroaryl radical, each of which maycontain 0, 1, 2 or 3 substituents, where the substituents are eachindependently selected from the following list: substituents on carbon:halogen, cyano, nitro, hydroxyl, amino, —SH, alkyl, alkenyl, alkynyl,haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, halocycloalkyl,alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxy,haloalkoxy, cycloalkoxy, halocycloalkoxy, alkenyloxy, alkynyloxy,alkoxyalkoxy, alkylamino, dialkylamino, alkylthio, haloalkylthio,alkylsulphinyl, haloalkylsulphinyl, alkylsulphonyl, haloalkylsulphonyl,trisilylalkyl or phenyl, substituents on nitrogen: hydrogen, —C(═O)H,alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl,cycloalkyl, halocycloalkyl, alkylcycloalkyl, cycloalkylalkyl,alkoxyalkyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl,phenylsulphonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,haloalkoxycarbonyl, cycloalkoxycarbonyl, —C(═O)NR³R⁴, phenyl or benzyl,Z⁴ is SH, C(═O)H, C₇-C₈-cycloalkyl, C₇-C₈-halocycloalkyl,cycloalkylcycloalkyl, halocycloalkylalkyl, cycloalkenyl,halocycloalkenyl, C₄-C₆-alkoxy-C₁-C₄-alkyl, C₃-alkoxy-C₂-C₄-alkyl,alkoxyalkoxyalkyl, alkylthioalkyl, alkylsulphinylalkyl,alkylsulphonylalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, cycloalkylaminoalkyl, C₄-C₆-alkylcarbonyl,haloalkylcarbonyl, cycloalkylcarbonyl, cycloalkoxycarbonyl,cycloalkylalkoxycarbonyl, cycloalkylaminocarbonyl, haloalkoxyalkyl,C₅-C₆-hydroxyalkyl, C₅-C₆-alkoxy, C₅-C₆-haloalkoxy, cycloalkoxy,halocycloalkoxy, cycloalkylalkoxy, alkenyloxy, haloalkenyloxy,alkynyloxy, haloalkynyloxy, alkoxyalkoxy, cyanoalkoxy,haloalkylcarbonyloxy, cycloalkylcarbonyloxy, alkylcarbonylalkoxy,C₅-C₆-alkylthio, C₅-C₆-haloalkylthio, C₅-C₆-alkylsulphinyl,C₅-C₆-haloalkylsulphinyl, C₅-C₆-alkylsulphonyl,C₅-C₆-haloalkylsulphonyl, cycloalkylsulphonyl, tri(C₃-C₄-alkyl)silyl,alkylsulphonylamino or haloalkylsulphonylamino, Z⁵ istri(C₂-C₄-alkyl)silyl, benzyl, phenyl, SH, C₅-C₆-alkoxy,C₅-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₅-C₆-alkylthio orC₅-C₆-haloalkylthio, Z⁶ is SH, cycloalkylcycloalkyl ortri(C₃-C₄-alkyl)silyl, Z⁷ is alkenyl, alkynyl, haloalkyl, haloalkenyl,haloalkynyl, cycloalkyl, halocycloalkyl, alkylcycloalkyl,cycloalkylalkyl, cycloalkylcycloalkyl, alkylsulphonyl, C(═O)H, benzyl orphenyl.
 11. A method for controlling phytopathogenic harmful fungi,comprising applying a compound according to claim 1 to thephytopathogenic harmful fungi and/or a habitat thereof.
 12. Acomposition for controlling phytopathogenic harmful fungi, comprising atleast one compound according to claim 1 and one or more extenders and/orsurfactants.
 13. The compound according to claim 1, capable of beingused for controlling phytopathogenic harmful fungi.
 14. A process forproducing compositions for controlling phytopathogenic harmful fungi,comprising mixing a compound according to claim 1, with one or moreextenders and/or surfactants.
 15. The compound according to claim 1,capable of being used for treatment of transgenic plants.
 14. A processfor producing compositions for controlling phytopathogenic harmfulfungi, comprising mixing a compound according to claim 1, with one ormore extenders and/or surfactants.
 15. The compound according to claim1, capable of being used for treatment of transgenic plants.